S7E10 – Build the Right GTM Engine: Hiring, Structure & Growth for SaaS Founders with Christopher Gannon

In a world where anyone can generate a “perfect” email with AI, does perfection even matter? According to Christopher Gannon, founder of Captivate Talent, what truly matters are the fundamentals: relationships, brand, and aesthetics. In this episode of the Grow Your B2B SaaS podcast, hosted by Joran from Reditus, Chris breaks down how startups should think about hiring go-to-market (GTM) talent, structuring teams, leveraging AI, and expanding into the US. This article summarizes their conversation into clear, actionable insights every founder should know.

From Filling Seats to Building Engines

Chris Gannon has spent most of his adult life in recruiting. Early in his career, hiring was primarily about filling seats to meet aggressive headcount goals. That changed when he joined a high-growth startup as Head of Talent, where leadership encouraged a more human-centered approach. He realized that the true goal wasn’t simply to fill roles; it was to align the right person with the right company. This alignment creates a powerful growth loop: happier employees, better performance, and sustainable business success. This belief led Chris to found Captivate Talent, a firm dedicated to helping startups build and scale revenue teams with precision and humanity, not just volume hiring.

When to Make Your First GTM Hire

For early-stage SaaS founders with less than $1M ARR, one of the most common questions is when to make your first GTM hire. Chris’s answer is simple: you should be pulled into that hire. If your calendar is packed with demos, pitches, and customer conversations to the point where you can’t meet your product team, it’s time to hire. But if you haven’t yet sold the product yourself, it’s too early. He often tells founders, “You’re not ready for us yet.” Founders should first sell the product themselves to understand market nuances and refine the messaging. Selling it yourself allows you to build a repeatable playbook that future hires can follow. Skipping this step leads to confusion and poor onboarding.

The Reality of Early-Stage Onboarding

At early-stage startups, onboarding is often limited. Chris jokes, “Here’s your laptop. Here’s the Google Drive. You’re in the right Slack channels. Payroll should be set up.” The best teams may have a detailed Notion workspace or a library of recorded customer calls, but even these assets can’t replace first-hand experience. Recording every customer call is essential. These recordings serve as training materials for new hires, improve messaging, and provide insights into customer pain points.

Who to Hire First: A Self-Assessment, Not a Playbook

There’s no universal answer to who your first GTM hire should be. It depends on your product, market, and personal strengths. Some businesses need a marketing lead who can build scalable systems, while others need a salesperson experienced in complex enterprise deals. Chris recalls a mistake from his own experience: hiring a sales and marketing person early so he could focus on administrative work like bookkeeping. In hindsight, he realized he had outsourced his superpower. The lesson is to never outsource what you’re best at. Rather than following someone else’s playbook, founders should start with self-assessment and hire to complement their weaknesses.

The Goldilocks Problem: Overhiring and Underhiring

Founders often make two mistakes when hiring for GTM roles: overhiring or underhiring. Overhiring happens when a startup brings in an expensive CRO or VP from an investor’s network, expecting them to instantly deliver growth. These executives may open doors early on but often struggle to execute at the scrappy, early-stage level. Underhiring happens when founders rely on junior SDRs to drive critical motions, like entering the US market. As Chris says, “Your strategy to enter the most competitive market in the world is going to be rested on a 24-year-old’s shoulders?” The solution is to find the balance. Define what outcomes you want to achieve in the next 12 to 18 months and hire someone capable of delivering those outcomes.

Design the Role Around Outcomes, Not Titles

Titles are irrelevant in early-stage startups. What matters are the outcomes you expect and the skills required to achieve them. Chris advises founders to define success over 12 to 18 months, reverse-engineer the job description from those goals, and let the title emerge naturally. Avoid ego-driven title negotiations on both sides. Function and results should always come before form and prestige.

Stay Involved and Leverage Call Libraries

Founders should remain closely involved in GTM activities for as long as possible. By recording and analyzing customer calls, they can build a library of insights that becomes invaluable for onboarding and continuous improvement. Reviewing transcripts and identifying common themes helps the team evolve messaging and product positioning over time.

AI Is Reshaping GTM Roles But Don’t Be Fooled by Titles

AI is rapidly transforming GTM functions. New titles like “GTM Engineer” are emerging, but Chris warns against being distracted by labels. Many companies use this title for traditional roles in sales, marketing, or RevOps that simply require AI proficiency. Captivate Talent has developed a rubric to assess AI fluency. A year ago, asking “Do you use ChatGPT?” was enough. Today, baseline usage is assumed. The most valuable hires are transformative, those who deploy AI into workflows, measure outcomes, and continuously iterate. Chris estimates that only 1 to 2 percent of candidates today fit this transformative profile. As one AI summit speaker said, “If you don’t have a seat at the table, you’re on the menu.” It’s no longer enough to use AI; you must prove the impact it creates.

In an AI World, Human Advantages Become More Valuable

As AI-generated messages flood inboxes, differentiation returns to human fundamentals: relationships, brand, and aesthetics. “In the world where everyone could write a perfect email, does the perfect email even matter? It doesn’t,” Chris says. The winners are those who turn digital interactions into genuine relationships and revenue. Despite AI-driven efficiencies, there’s still more demand for skilled GTM talent than supply, especially in the B2B tech segment.

Entering the US: Strategy, Commitment, and the Burn the Boats Mentality

Expanding into the US is one of the toughest challenges for European founders. Chris has seen multiple failed attempts but also several success stories. Roughly 30 to 40 percent of Captivate’s current work involves helping European founders build US GTM teams. His advice is clear: don’t test the US market with a single hire. Instead, be pulled in by customer demand. Start selling into the US from your home base, then commit fully once you see traction. Founders should personally lead the charge, spending significant time in the market to understand customers directly. US expansion is capital-intensive; it requires a full GTM strategy covering sales, marketing, and customer success. Chris calls this the “burn the boats” mentality: no turning back once you commit.

Why the US Needs a Different Strategy

Even if your product is in English, the US market is distinct. For lower-ACV or PLG products, remote expansion can work initially, but as deals get larger, customers expect local presence and dedicated support. US customers and candidates can sense when a company isn’t fully committed. Hiring one local person without a broader plan signals a lack of seriousness. Successful founders build intentional, full-scale US operations with proper structure and investment. Chris also warns against using foreign logo credibility. Winning a small deal in a European office of a global brand doesn’t carry weight with decision-makers at US headquarters.

Advice for US Companies Entering Europe

For US companies expanding into Europe, the same principle applies: commit. Spend time in-market, build relationships, and work with experienced local recruiters and legal counsel. Laws and work cultures vary significantly by country and even by state, so localized expertise is essential. Cultural nuances also matter. Chris recalls a company that named all its conference rooms in its native language. A US hire felt excluded and couldn’t even find the right meeting room. Cultural adaptation builds trust and inclusion.

Misconceptions: Cost and Culture

The two biggest misconceptions about US expansion are cost and culture. US GTM talent is more expensive than most founders expect, and compensation structures differ. Chris advises increasing your budget by at least 20 percent. Culturally, founders must adapt their approach. American employees often take fewer vacations, and their expectations around feedback, performance, and recognition differ from European norms. Sensitivity to these cultural differences helps attract and retain great talent.

The Future: Change Is the Constant

Looking ahead, founders should prepare for continuous change, especially driven by AI. The traits of top GTM performers are shifting rapidly, and AI competency is already influencing executive-level hiring decisions. Founders must understand this evolving landscape to stay competitive.

From 0 to 10K MRR: Discipline and Community

In the earliest stage, success comes down to discipline and persistence. Founders must stay committed even when progress feels slow. Building a peer network is invaluable because friends and family may not understand the entrepreneurial journey. Show up in communities to learn and give value, not to sell. That’s how meaningful connections are built.

From 10K MRR to $10M ARR: Hire Ahead and Hire Right

As your company grows, hiring decisions become even more critical. Chris advises founders to hire ahead and hire right. Don’t lose great candidates over small compensation gaps; top performers deliver exponentially higher ROI. He also stresses the importance of hiring for where you’re going, not where you are. If your goal is to grow from $10M to $20M ARR, bring in leaders who have already done that journey successfully.

The Lines That Stood Out

“In the world where everyone could write a perfect email, does the perfect email even matter? It doesn’t.” “If you don’t have a seat at the table, you’re on the menu.” “You have to be pulled into it.” “Titles in early-stage startups mean nothing.” “Hire where you want to go, not where you are.” “Burn the boats.”

Final Takeaways for Founders

Founders should start by selling their own product to build firsthand understanding of their market. Record every customer call to create onboarding materials and institutional knowledge. Define clear outcomes over the next 12 to 18 months and hire backward from those goals. Avoid overhiring senior titles or underhiring for key roles. Expect AI fluency as a baseline, but look for transformative operators who can prove results. As AI-generated content floods the market, relationships, brand, and aesthetics will be the lasting differentiators. When expanding into the US, commit fully, don’t test the waters. Budget realistically, adapt culturally, and lead with presence. Build genuine networks, show up to contribute, and as you scale, always hire for the stage you’re aiming to reach.

Key Timestamps

• (00:00) The Perfect Email Myth: Why Human Connection Still Wins
• (00:55) Meet the Masters of B2B SaaS Growth
• (01:31) Why Headcount Won’t Scale Your SaaS Revenue
• (01:51) From Filling Seats to Building a GTM Powerhouse
• (02:10) The Birth of Captivate Talent: A Founder’s Bold Pivot
• (03:33) The $1M ARR Question: When to Hire Your First GTM Pro
• (03:50) The Founder’s Dilemma: Sell It Yourself or Hire Early?
• (04:58) The Brutal Truth About Early-Stage Onboarding
• (05:39) Who Comes First—Sales or Marketing? The Real Answer
• (05:54) Never Outsource Your Superpower
• (07:20) Overhiring vs. Underhiring: The Startup Goldilocks Problem
• (08:16) The Rolodex Trap: Why Big Titles Burn Startups
• (09:22) Forget Titles—Hire for 12-Month Outcomes Instead
• (10:15) Inside the Ideal GTM Team Structure for SaaS Growth
• (11:08) The Secret Weapon: Your Customer Call Library
• (11:39) AI Is Taking Over GTM (But Here’s the Catch)
• (12:11) Beyond ChatGPT: How to Spot True AI Fluency
• (13:48) Reditus Break: The Affiliate Engine Powering B2B SaaS
• (14:11) How to Measure Real AI Impact in Your Workflows
• (15:06) “At the Table or on the Menu?” AI Skills That Protect Your Career
• (15:44) The Truth About GTM Hiring in a Post-Layoff World
• (16:24) Why Relationships Beat Perfect AI Emails Every Time
• (17:44) The Costly Mistake: Hiring an SDR for US Expansion
• (18:10) The Founder-Led Playbook for Cracking the US Market
• (19:09) The Full-Stack Expansion Model Every SaaS Needs
• (20:22) Stop “Testing” the US with One Hire—Here’s Why
• (22:08) PLG vs. Enterprise: When Remote Expansion Stops Working
• (23:33) Why Big Logos Abroad Don’t Impress US Buyers
• (24:24) US to Europe: How to Win with Local Talent and Presence
• (25:29) The Hidden Legal Maze of US Hiring
• (26:26) The Real Cost of US Expansion (and Cultural Fit)
• (28:34) The Culture Clash: Vacations, Burnout, and Commitment
• (29:21) Burn the Boats: The Only Way to Win in the US
• (30:12) The Future of GTM: How AI Is Rewriting Hiring Rules
• (31:16) From 0 to $10K MRR: Discipline Over Everything
• (32:47) From $10K to $10M ARR: Hire Ahead and Pay for Talent
• (36:49) Connect with Christopher Gannon and Captivate Talent

Transcription

[00:00:00.000] – Christopher Gannon

In the world where everyone could write a perfect email, does the perfect email even matter? It doesn’t. The reality is this relationships will matter. Brands will matter. Esthetics will matter. With all this technology being deployed, we’re actually going back onto some of the core things that make go-to-market special being the most important things. At the end of the day, even titles in early-stage startups mean nothing. You could say it’s a CRO, you could say it’s a VP of Sales, you could say it’s a Senior Account Executive. At the end of the day, we need to look at what that person needs to achieve, match it up with the skill sets, and the title fall in place later. If you’re a founder and you look at your calendar and you have no time left, can’t find time to go meet with your product team because you’re too busy with sales calls, demos, client pitches, and customers, that’s when you have to really look at starting to hire your first go-to-market person.

[00:00:55.660] – Joran

When scaling your B2B SaaS, we often talk about incorporating frameworks, trying out different acquisition channels, or we want to scale without hiring more people. However, this is definitely not always possible and the best way to grow. Often, the real engine behind scaling is the go-to-market talent you hire, how you structure the team, and the timing of all of it. Today, we’re going to talk about building your go-to-market engine by hiring the right people who can help you to start the engine or take a step further. My guest is Christopher Gannon, the founder of Captivate Talent. His company has helped startups to build and scale their revenue teams with a human-centered precision. Welcome to the show, Chris.

[00:01:31.320] – Christopher Gannon

Hey, Joran. Thanks so much for having me. We believe, too, that you should grow efficiently and not just hire a bunch of people because that creates usually pretty bad outcomes.

[00:01:40.600] – Joran

Nice. But in the end, you’re going to need people to maintain all the machines you’re going to build all the other machines you’re going to build. You can’t do it without people.

[00:01:48.180] – Christopher Gannon

That’s our hope of the future. I think that’s many people’s hopes.

[00:01:51.180] – Joran

We like to dive right in and start at the basics. You build out, go to market, and revenue teams at high-growth SaaS companies. Can you take us to the moment you realized recruiting wasn’t just about filling seats, but about building the right engine for growth? And then what changed for you in that period and how you’re looking at hiring now?

[00:02:10.890] – Christopher Gannon

I’ve been in recruiting pretty much my entire adult life, and I’m on the other side of 40 now. For the first half, recruiting was all about filling seats. The places I worked, you had goals and targets, and the only outcome that you were looking for was to fill a seat. Then something started to change. I was fortunate. The second time I was a head of talent for a high-growth startup, I had some great leadership around me. They started talking to me about more focusing on the human element. They knew when they hired me, I had that inside of me, but that wasn’t necessarily how I was taught to do recruitment. So once I spent a little bit of time there, I had this aha moment, and that’s where I started Captivate Talent, where we want to get somebody in a seat, but we really need to make sure that it’s the right person. And not only it’s the right person for the company, but it’s the right company for the person, because that will a nice flywheel, a really happy experience. It’ll be more business for us and help the company grow truly, versus just putting somebody in a seat which will turn over and not be a great hire for them.

[00:03:11.450] – Christopher Gannon

And then they’re just in that hamster wheel of just trying to always catch up.

[00:03:14.900] – Joran

Nice. I think that’s a good phrase, get the right person for the company in the right company for the person. It’s a two-way street.

[00:03:21.580] – Christopher Gannon

It’s really important that you look at it as a two-way street. It has to be a match on both sides. We work most of our adult lives. Regretfully, most of us are going to to do it. You have to be somewhat satisfied with what you do and where you work.

[00:03:33.700] – Joran

Let’s take it to the beginning. For a SaaS founder who hasn’t made their first higher yet, product net growth is what everybody is achieving or going for. So early stage SaaS founder, under one million ARR, when should they even think about hiring their first go-to-market person?

[00:03:50.280] – Christopher Gannon

I’m fortunate enough where I’m on the front lines of Captivate Talent in the sense of interacting with the early stage founders. That’s a lot of the conversations I’m having during the weekend. Trouwyn, to be honest with you, half of those conversations end in, you’re not ready for us yet. You should go talk to these people or work with this consultant. Or honestly, as a founder, you just have to go sell your product more and make sure that you really have a great product and product-market fit. The signals we look for, if you’re a founder and you look at your calendar and you have no time left, can’t find time to go meet with your product team because you’re too busy with sales calls, demos, client pitches, and customers, that’s when you have to really look at starting to hire your first go-to-market person. You have to be pulled into it versus trying to kick in the door. That’s how we view actually also entering the US. There are similar motions at slightly different scales, but you have to be pulled into this type of hire because if you’re a technical founder all the out there and you just hate sales and you never want to sell your own product, you’re not going to learn the nuances of what the market’s looking for, and you’ll never be able to build your product the right way.

[00:04:52.960] – Christopher Gannon

You’ll never be able to build a playbook to pass on to those founding go-to-market hires to sell your product the right way.

[00:04:58.890] – Joran

You have to sell yourself. You to do things yourself first. It will also help with onboarding, right? If you already know what is working and what isn’t, do you see a lot of advantages there as well?

[00:05:09.440] – Christopher Gannon

Onboarding at an early stage startup, let’s not even call it onboarding. Our process is like, here’s your laptop, Here’s the Google Drive. Can I put you in all the right Slack channels? And hopefully, it set you up on payroll. That’s what onboarding looks like at the early stage. The best of the best, maybe they have a really nice Notion doc built out and they have a lot of customer calls that this person could look at first. But Again, that last part, if you’re not doing any of the sales yourself, you’re never going to be able to onboard that person effectively into your go-to-market process.

[00:05:39.000] – Joran

Makes sense. You mentioned you have to be pulled into it, right? Sometimes maybe I can imagine early stage founders don’t know who they need to hire. Do they want to replace, for example, them doing the sales or them doing the marketing? Any advice, like what person you need to hire first?

[00:05:54.420] – Christopher Gannon

Yeah. Look, if you’re a founder and you’ve built a really great marketing engine and you can spike in those areas because marketing right now is very systematized and there’s a lot of technology you can throw at it. But maybe that’s not or your first hire is. Maybe you are hiring somebody who has some enterprise sale experience because you realize once you’re getting into these multi-threaded, multiple decision-maker types of deals, things fall off the tracks a little bit. You have to really look at a self-assessment of what you’re really good at and what you’re really bad at. I made the mistake myself. My third hire at Captivate Talent was a sales and marketing person. They were great. They were just the wrong person for us at the wrong time. And the craziest thing, six months into this person’s hire, I realized that I was outsourcing the stuff I was really good at. So I could go spend more time doing administrative things. I think one of the things was bookkeeping. So instead of outsourcing my bookkeeping for $500, $600 a month at that point, I was outsourcing my superpower. Founders have to be careful, especially with all the playbooks out there, all the blogs out there, all the podcasts out there, that you’re doing a true self-assessment and you’re prescribing the right medicine for yourself, not just what somebody else is doing, because your challenge or what you need for your org is going to be different than everyone else.

[00:07:12.850] – Joran

It’s interesting you made that mistake, as a hiring person, what other mistakes you see founders make when hiring? I’m curious.

[00:07:20.910] – Christopher Gannon

We call it Goldilocks. They either overhire or underhire. We can tell on the first call with them if they’ve already made a hire and it didn’t work out which one they made, because then They go to the other extreme. Founders get some advice from a board member, Oh, you need a CRO or a VP right now? And they get this person from their boards network or their investors network, and they come from the industry and they have all these contacts. They have 25 years of experience. That’s one big mistake. That’s actually a really expensive mistake because that costs you not only a ton of money, because those people in the US, at least 300, 400, 500K potentially, the capital that you’re going to burn, but they’re also going to cost you a ton of time. It will take you a while to realize that person’s not going to learn. They come door, they’re going to just work the Rolodex. People say, Oh, we want to hire with a Rolodex, which is ironic because we’re talking about this antiquated piece of office equipment that doesn’t exist anymore. They get a couple of meetings, and it seems really exciting because it’s their contacts and it’s their friends from the industry that they’ve known, and it gets really exciting for the founder.

[00:08:16.710] – Christopher Gannon

But that Rolodex gets burned up quickly. Then all of a sudden, you have somebody who’s not doing the true, gritty part of the early stage Coda market process that’s in your organization, burning up a ton of capital. Then what happens is they go in the other direction and we’ll get founders that are like, I need to hire an SDR. We’re entering the US market, we want to hire an SDR. I have to look at them and being like, Okay, your strategy to enter the most competitive market in the world is going to be rested on a 24-year-old’s shoulders who’s sitting at home in their mom’s basement watching Netflix half the day. How’s that going to work? It’s about threading the needle and assessing the right person at the perfect time to hire them.

[00:08:50.940] – Joran

Yeah. That sounds simple, right? But to find the right person for your right time, I think that’s… We even made the mistake ourselves where I hired a growth person, was last year, I think, where it was way too early, where I was like, Okay, at one point, I knew it didn’t work out because I had no processes. We didn’t have product-market fit, so I was keeping him busy, but at the wrong time. It’s easy to have the wrong time and maybe to hire somebody that doesn’t fit it with your stage right now.

[00:09:22.400] – Christopher Gannon

What we recommend, and we do this with all of our founders that we work with, is we say, All right, 12 to 18 months, what do you want this person to achieve. Then we reverse engineer job description off those objectives. Because at the end of the day, even titles in early stage startups mean nothing. You could say it’s a CRO, you could say it’s a VP of Sales, you could say it’s a Senior Account Executive. At the end of the day, we need to look at what that person needs to achieve, match it up with the skill sets, and the title fall in place later. People get so stuck with titles sometimes because it’s an ego thing on both sides. You really have to look at what the function is, what the company needs, needs and hiring the right person to fit that, and who cares what their title is.

[00:10:03.490] – Joran

When we take it then one step further, at one point, you’re going to structure the team and create a go-to-market team. Is there a structure you would recommend people you need to have, or does it depend on the type of company?

[00:10:15.480] – Christopher Gannon

It depends on the type of company and your product at the end of the day. Again, if the founder has some go-to-market experience, can they get a little farther along than a true technical founder that doesn’t have a go-to-market experience? You could lean both ways for that. But again, at the end of the day, there’s There’s a company out there, two founders, they’re both technical founders. The company’s named Typeful founder. They do sales training. The reason they got their product so far along is because they had to figure out how to sell their product themselves. It was through all those challenges and all those nos that they figured out how to retool and build their product in a better way, in a way that the market wanted. Versus if they farmed that out to a salesperson, they probably wouldn’t have gotten those insights early on. Even if you are a technical founder, that you feel like, Hey, I’m at the point where my calendar is too busy. I still need to be involved in go-to-market, but now I need an extra set of hands here. Yeah.

[00:11:08.760] – Joran

I think if I can just give an advice here, if you are having the calls yourself, if you can record them, if you’re going to hire somebody, at least you can have him or her watch all the recordings and learn from all the calls you’ve been doing before they actually joined.

[00:11:23.240] – Christopher Gannon

Yeah. Like day one, if you’re not recording all your customer calls for whatever reason right now, start, please. I can’t remember the last time I’ve jumped on a call where somebody wasn’t recording it, but please record all your calls because that’s valuable information for the salespeople. Yeah.

[00:11:39.820] – Joran

Not all calls are recorded. You get fed up with a notetaker sometimes in there. So one time I started blocking them, but I did edit them back in because in the end, it could also help with your positioning. If you get the similar questions all the time, you feed the transcripts into any AI, and then from there, you can have a-The library. Exactly. So definitely do it. I guess this This is one way of AI changing SaaS companies, but I actually wanted to go towards AI and the functions of the go-to-market people. What is the impact of AI?

[00:12:11.840] – Christopher Gannon

We’re seeing a rapid change of what the go-to-market landscape looks like and what those functions look like. The funny thing is, everyone’s talking about this role, GTM engineer, and we ran a search back in June, and there was about 250 some odd people in the US with the title GTM engineer. So it was this big hot topic, but none of these people actually really existed when we looked at the market. And now in September, we ran that same search again, and that number has tripled almost. So that is a growing function, but we’re seeing it being used as also a rapper for roles where Every function that we’ve talked to that we cover, which is sales, marketing, CS, and RevOps, we’ve heard the GTM engineer title, Spike Up. It’s a rapper for an AI-enabled individual in that function. We’re cautioning our founders, don’t just throw this this rapper title at a function, understand that you are looking maybe for this traditional demand gen manager. That’s what the person’s core duties were, but you’re looking for them to be AI-enabled. We had to build a rubric internally, which we’ve now pushed out externally, on how we’re assessing different levels of AI fluency and competency.

[00:13:19.620] – Christopher Gannon

Where a year ago, it’s like, Hey, how are you using ChatGPT? Are you using it? That was the basic question people would use in interviews to say, Oh, is somebody AI-competent? Where Now, today, if somebody’s not baseline doing those things, they’re not even relevant for a lot of the companies that we’re talking to because the companies that we’re talking to, the best ones, they’re looking for people that are not only adaptive, but they’re looking for people that are transformative with their ability to deploy AI into their function. So the roles are rapidly changing.

[00:13:48.670] – Joran

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[00:14:11.440] – Christopher Gannon

It’s crazy because it reminds me when social media started becoming a thing that we were using in B2B. We started seeing this title pop up, Social Media Manager. People were like, I want four or five years of somebody with social media experience. The reality was a year or two into Instagram, that was somebody who maybe just knew how to post a lot of pictures. Those people didn’t exist on the market. We’re seeing that now. 1-2% of candidates in the market today are truly transformative with their AI. They have been able to deploy, measure outcomes, adjust those outcomes, and implement again into the success of their organization. A few people have that now, but we are seeing now we are far enough along where people actually have been able to measure their success on how they’ve deployed AI. It might only be 6-12 months of data, but those candidates are starting to come into the market Yeah, that’s interesting.

[00:15:01.180] – Joran

Not just being able to use it, but to show the output and what they learned to make the input better.

[00:15:06.900] – Christopher Gannon

I was at an AI summit last week, and the mindset was, if you don’t have a seat at the table, you’re on the menu. I would assume that almost every founder listening to this podcast is deeply immersed in how they’re using it. But that’s what we’re starting to see demanded from the talent market, too. You can’t just be somebody that’s sitting on your basic ChatGPT account and asking it to write emails. You have to be tooling around on your own and really being able to find applications for building better workflows.

[00:15:32.760] – Joran

Yeah, it’s nice. If you don’t ever see it on table, you’re on the menu. I think that goes for a lot of employees, right? A lot of people. Do you also see that a lot less people are being hired now in go-to-market teams?

[00:15:44.370] – Christopher Gannon

There’s a lot of misnoms. I would say it’s the media. The media, when Microsoft lays off 2,000 or 3,000 people, it’s like, Oh, there’s layoffs, tariffs, less of a job market. We’re very focused on B2B tech, early to growth stage startups. In our world, more people are getting hired. While there are strategies deployed of one to many where you can do more with less people, at the same time, the amount of opportunity that’s being created in the market is 10X. There’s actually significantly more demand in the market for talent than supply right now.

[00:16:17.180] – Joran

Indian demand changes. People are looking for hidden gems, leveraging AI, and not on the menu at the moment.

[00:16:24.720] – Christopher Gannon

Yeah, you want to make sure you’re not on the menu. At the end of the day, the funny thing in go-to-market space with all the technology, I believe the head of go-to-markets for startups at OpenAI. He had a quote at this at the seminar that said, In the world where everyone could write a perfect email, does the perfect email even matter? It doesn’t. The reality is this relationships will matter. Brands will matter. Esthetics will matter. With all this technology being deployed, we’re actually going back onto some of the core things that make go-to-market special being the most important things. So anybody could be a great email writer, but it’s the person that could take that great email and carry through a relationship, they’re going to win at the end of the day.

[00:17:09.680] – Joran

It makes sense. In the end, all channels get cluttered, and especially, I guess, if it’s going to be AI generated everywhere, then you need to stand out in a different way. And the only way to do it is to become human again.

[00:17:21.060] – Christopher Gannon

Yeah. We all look at our own inbox and we see the AI slop and garbage coming through every day. How are you breaking through the noise? We’re seeing people in the go-to-market space. These toolings and these workflows, they’re really, really important to increase efficiency. But we also need people that are really talented to carry those efficiencies through to the next level and truly build companies and grow revenue.

[00:17:44.350] – Joran

Yeah, it makes sense. We’re going to dive in a completely different topic. You touched upon it a little bit. We spoke at SaaS Talk quite a bit, and I think one of the topics you had with SaaS founders was going to the US and then scaling to the US. You mentioned that the biggest mistake is hiring an SDR and relying on the SDR. For a SaaS founder in Europe looking to scale to US, how should they tackle or how should they go about it?

[00:18:10.520] – Christopher Gannon

This is, again, something I lived through myself. I was in a failure to launch business in the US twice, and there was a lot of mistakes made. When I came to Captivate Talent, I had a little bit of a network in Europe, and we continued to build that network. Now, 30 to 40% of our business at any given time is people entering the US from a go-to-market standpoint. It is one of the most challenging motions a founder of a foreign entity could go through. There are so many hurdles and mistakes that could get made that they have to overcome to build that. We doubled down on how to help them and advise them to get into that market. One of the biggest mistakes we see being made is the US says, You need to have a burn the boats mentality. When you land in the US, you can’t land softly and you can’t think about, Oh, I’m going to hire and a junior AE, and they’re going to do some sales and we’re going to see how the market reacts to it. You have to be in a state where you’re being pulled into the US market.

[00:19:09.900] – Christopher Gannon

From your home base, you have to start getting customers in the US. You have to figure that out on your own. Once you do that and you have expansion product market fit, that’s when you have to build out a true US expansion strategy. That doesn’t mean hiring one person. It’s an extremely capital-intensive exercise. That’s usually when we see founders going for funding again when they think about entering the US. You have to deploy a true strategy that’s not only around a person, but it’s around the whole function. Not only are you going to hire a salesperson, but how is your whole marketing organization being realized? Are you hiring marketing people in the US? What about your CSMs? Your team back in London or Serbia or Stockholm, wherever they might be, might be okay with being on calls late at night for US clients and customers for the first few months, but eventually that’s going to break. So You can’t have a customer or client on the West Coast at 2: 00 in their afternoon being like, Oh, I need help with this. I have a problem. They’re getting a response, Oh, we’ll be back online tomorrow morning.

[00:20:10.460] – Christopher Gannon

We’ll message you at 4: 00 AM your time with a resolution. That’s not going to work. The US has to be a truly baked-out strategy of how you’re entering that from a full go-to-market perspective, not just making a higher or two.

[00:20:22.380] – Joran

I’m going to put my founder hat on. People want to see it as an experiment. Everybody wants to go to the US. I think that’s one language, big market, easier than Europe when you look at how we have to sell here. It sounds good, but it also sounds big and expensive. I know people are thinking, Well, I might just do start with one higher or I do start maybe smaller. Is there a way where you can break things up while having, I guess, the big expansion strategy so you don’t have to burn a lot of money at the beginning?

[00:20:52.980] – Christopher Gannon

The test usually doesn’t work for a few reasons. The test with a higher, I should say. We advise companies, the founder has to start trying to sell into the US. In your home country, the founder might have gotten out of sales. They’ve built a team, that’s great. But they have to be the one that’s stewarding this expansion. That means getting on a plane, spending time and selling into that market yourself. We always say that, hey, founders that end up committing to this market by moving here, they tend to be significantly more successful than ones that don’t. It’s because they could iterate. They can understand what their client here needs, maybe how their customer is different here a lot quicker. If you hire a mid-level AE, are they going to understand all the pricing challenges? Are they going to understand all the product challenges? Are they going to be able to translate that to your product team, your customer success team, your executive team on a consistent basis and at a high level? The chances are probably not. We think that the founder has to lead that expansion. And once they do get a little bit of product market fit here in this market, that’s when you have to deploy that true strategy of expansion, not just the hire or to.

[00:21:57.390] – Joran

We’re going to be devil advocate here a bit. We all speak English in Europe, right? You speak English? Yeah. Why should we have a different strategy for US versus whatever we do in English in Europe?

[00:22:08.040] – Christopher Gannon

I think there are some products, especially when you look at lower ACBs and stuff like that, that you can get by not physically expanding a footprint into the US. There’s probably a certain type of critical mass that you could hit, especially with lower-level products further along. Plg motions, self-serve, things that maybe take a light assist for onboarding or implementation or support. Those things you could expand it to the US from your own country. But once you start going up market quite a bit, that’s when things get really tricky. That’s where we believe that you truly have to have a team that’s dedicated here to your customers here, and they need to see your commitment to this market. There’s a lot of companies that try to enter here, and customers will be weary and look at, is your support team here? Is your sales team here? Candidates are the same way. If they see that you’re just trying to hire one person here, they might figure out quickly their experiment. In seven or eight months, if you don’t like how things are going, you’re just going to retreat, pack up, and close it down, and they’re going to have to go look for a job again.

[00:23:06.860] – Christopher Gannon

That’s why we caution, when you’re ready to go, when you’re hitting, again, critical mass of how far your product can go, is being sold from your home country, that’s when you have to take that big jump.

[00:23:16.940] – Joran

Yeah, in the end, the culture is going to be different. During calls, I do demos with US companies. I get more questions like, How long have you been around? But your team, they’re qualifying our company indeed. If we would stick around and we’re not just going to enter and leave. I see your point.

[00:23:33.280] – Christopher Gannon

When I talked about those failure launches, it’s a lesson I learned myself. I was that experimental employee. I knew they weren’t pouring the right amount of resources. They were saying, Oh, just go on our brand name, just go on our brand name. Look at all these logos we have in the UK. The reality is you might be in your home country and be like, Look, we have Johnson & Johnson in Lithuania. I don’t know if Johnson & Johnson has an office in Lithuania, but I’m sure it’s maybe at most 100 people. Johnson & Johnson out here in New Jersey headquarters doesn’t care about that office. They don’t care about your brand name. It means nothing to them. It’s an entirely different company. They’re looking for people who know this market and will commit to this market, not to have sold an offshoot into another market.

[00:24:15.080] – Joran

Let’s turn it around. We also have US listeners. What advice would you give them if they want to go outside of US and make their way to Europe? Any advice there?

[00:24:24.060] – Christopher Gannon

Find a great recruiter that I can recommend in Europe to help you establish your beachhead there. The thing we’re really good at is going from Europe to the US. The thing we have no idea how to do properly is go from the US to Europe. At the end of the day, you have to commit to those markets. I’m in Europe a couple of times a year for a reason to show that we’re committed to that market and helping people cross over. It’s one of those things at the end of the day, we have so much technology that allows us to do calls around the world and everything, but you probably have to get on a plane and spend a lot more than you think.

[00:24:58.480] – Joran

Do more dinners, drinks, and chats.

[00:25:01.460] – Christopher Gannon

And long nights and times away from family, that’s the true commitment to entering a foreign market. Can’t do it from afar.

[00:25:08.750] – Joran

Yeah, nice. Going to Europe, it’s going to be super complicated for US companies because we have so many different languages, so many different cultures, even within countries. Of course, same as with US, but the difference are a lot bigger because we literally can’t understand each other if you just drive 200 kilometers or so miles.

[00:25:29.120] – Christopher Gannon

The tricky The great thing about the US is that we have 50 different states and they have 50 different sets of employment laws and labor laws. It’s the same as, Hey, you’re going to Europe, you have to set up 30 plus different entities for every country and learn different rules and everything. It’s the same here. If you put your business in New York versus Massachusetts versus Delaware, you’re going to encounter some slightly different labor laws. We always recommend, we have a really good lawyer or two that we’d point somebody in the right direction that is a pro in that type of expansion, getting on early because you don’t want to deal with the paperwork if you mess something up.

[00:26:04.290] – Joran

Yeah, it makes sense. This is, I guess, one misconception we have, right? It’s just one country, it probably has one set of rules. Are there any other misconceptions we have if we look at US as a whole or maybe just moving to US? I guess the other one was just hiring one person or too early or too young person. Any other things?

[00:26:26.360] – Christopher Gannon

There’s two things, cost and culture. Cost, the US more expensive. I don’t think they realize how much more expensive, especially on the go-to-market side of things. Sales people here, go-to-market people here, they’re paid a lot more, and their comp packages are a lot different than Europe. We always say, Whatever budget you think you have, make it more expensive and add 20% to it. That’s where you end up in the US when you start hiring people and building things. At the same time, culture is really underestimated. We think we can bring our culture, we could bring our DNA. This is a country of people who are resistant to other cultures. It is rooted in our history. We have shown time to time again in history that we don’t take the force of other cultures on. We think about that from an employee perspective, too. We had a customer back in our early days. They named all their conference rooms after things in their home country. When they expanded here, they spoke their native language a lot. We placed a candidate there and he said, I don’t think this is the right fit for me because I have no idea what conference room I even need to go into for a lot of my meetings because I don’t know what they mean.

[00:27:29.750] – Christopher Gannon

I At the end of the day, I feel like everyone’s talking about me if there’s no one speaking English in the office. The reality is the US, less than 50% of the people even have their passport. It’s not like Europe where you’re born with a passport. You can meet somebody that speaks a different language by, you said it, driving 100 kilometers in a different direction. There’s a lot of the US that’s not exposed to other cultures. You have to be careful and thoughtful about adapting to their culture and bringing pieces of your DNA over. There’s not a problem with that, but you cannot impose a culture onto a team or office that you hire. A native team or office, I should say, at least.

[00:28:04.120] – Joran

I think culture is also different. When I was leading the customer success team at Leadfeater, we had 30 people or even 32, I think, and I think 40%, 30% was in US. The other half was in Europe, which always was fun. But I had to force people in US to take a holiday. They were entitled to holidays. I can’t remember how many times I told them, take a holiday, don’t open up your laptop and do nothing. It was actually not possible. It was mission impossible.

[00:28:34.160] – Christopher Gannon

The work culture here is different. How employees view vacation or holiday is different. The joke we have is in August, our European clients disappear for a few weeks. We try to plan that in as best as possible because we know that’s going to be a revenue shift into different markets. It’s important. A founder spends meaningful amount of time here understanding not only the market, but employees that they hire here. We have a great client called Finout. They’re doing really well in the US. Roy, their founder, was on a plane every three weeks away from his family. He had a baby and he was on a plane two and a half weeks later. A lot of time spent away from home to truly understand the market, understand his team, and He built the right way here.

[00:29:16.240] – Joran

Yeah, this comes down to commitment. He committed to go to the US, so he knew he needed to be there.

[00:29:21.660] – Christopher Gannon

He deployed the burn the boat strategy. He had a truly actionable 6, 12, 18, 24-month plan to execute when he landed in the US. It wasn’t, let’s see how it goes in six months. That’s dangerous.

[00:29:34.900] – Joran

Is that an actual term, burn the boat strategy?

[00:29:37.980] – Christopher Gannon

Yeah, there’s back and forth. They say it was a Greek myth, but then it was one of the conquistadors when he landed in South America. He told his general, when they landed, burn the boats, because the only way we’re going home is through victory. That was the mentality that they had to win that battle. We view it the same way. The path of success is through victory, and you have to be committed to that victory.

[00:29:59.330] – Joran

There’s no way We’re going to start wrapping things up. We’re going to go to the final three questions. When we’re going to look into the future, what should SaaS founders prepare for in the next one, two, three years?

[00:30:12.350] – Christopher Gannon

Change. The challenge is, are we in a bubble or a renaissance right now? Change is happening quickly. The profile of what a top person in go-to-market looks like is changing rapidly. We’re trying to be ahead of that as much as possible, but we’re seeing that change quickly. For the first time, the thought was, Oh, all the low-level jobs, AI is coming for you. It’s game over. For the first time we saw an executive at a mature company at a CMO level, the decision that was made between the two candidates was who deployed and measured AI the best in the interview process. You’re thinking about how new we are into AI in the timeline. That change has happened already at the executive level, and it is happening. I think the biggest thing that founders need to What are you thinking about right now is how that change is going to impact them, their strategy, and the people that they’re going to hire.

[00:31:05.880] – Joran

When we’re going to take it into revenue stages, what advice would you give a SaaS founder who’s just starting out and going from 0 to 10K monthly recurring revenue?

[00:31:16.130] – Christopher Gannon

It’s back to that commitment, that level of commitment and desire to achieve something resonates through all levels. At that stage, you have to have that personal commitment and discipline. You have to understand what you’re doing is hard and no one’s going to care, but you have to get it done. Finding a network is really important for that early stage founder. It’s something that I didn’t do early on that I wish I did earlier is finding a group of people like me or like yourself that will maybe understand that because you go home, your family might not get it. Your friends that you had in primary school are probably going to understand it unless they’re doing the same thing. It’s really important you understand the commitment you have to go through and maybe find a network of other people that will understand that, too.

[00:31:57.310] – Joran

I’m personally involved in two communities, one in the Netherlands that’s focused and one with SaaS Talk, the SaaS Talk founder membership group, which has brought me so much value.

[00:32:05.840] – Christopher Gannon

I think it’s important that when you enter those networks, do not sell. If you’re entering those networks to sell, you’re going to lose in a You have to enter those networks, being able to listen, get advice, and hopefully bring advice and help other people. It’s really, really important that you do that because we see so many people come through these networks and they’re just trying to sell you. They get pushed to the side and nobody wants to talk to those people or give them any advice or help.

[00:32:32.710] – Joran

Yeah, and the more open you are, the more you show up to the event and things like that, the more you share, the more you’re going to get back as well. That’s definitely something I have learned. Nice. Let’s assume we pass 10K MRR and make a huge step towards 10 million ARR. What advice would you give a SaaS founder here?

[00:32:47.580] – Christopher Gannon

So higher ahead and higher right. These are all things I’ve practiced myself. So when I give this advice, I can be confident that I’m talking the talk and walking the walk in the world of go-to-market. If you have somebody great and you let $10,000 or $20,000 get in the way of you hiring somebody to look great, how that $10,000 or $20,000 can compound over time from an ROI perspective can be massive. I mean, even if you think of an AE with a million dollar quota, 10 to $20,000 could be the difference between finding that AE who’s going to blow out their million dollar quota and bring your company a million, a million and two, a million and five in revenue, or you find somebody that does $500,000 in revenue. It’s important that when you think about a couple of thousand dollars, we’re founders, we’re bootstrapped, we might not have a lot of funding, we’re trying to raise all these things, that money could be really impactful down the road for you. The other thing is also hire where you want to go, not where you are. If you’re at 8, 9, 10, and you want to go to 20, you have to find somebody that’s gone on that journey and that can take you on that journey again versus the person that, Look, our job is to mitigate risk.

[00:34:00.500] – Christopher Gannon

Somebody who’s never done that 10 to $20 million motion, they’re going to make a lot of mistakes. They might not understand the system and the processes that take. They might not have a hiring methodology to build a team to scale to that level. How much risk do you want to burden on yourself? How much of those mistakes are you willing to tolerate versus finding somebody who’s been on that journey successfully again?

[00:34:21.420] – Joran

All right. Makes sense. Good advice here. Let me try to summarize here. When we take it all the way to the beginning, get the right person for the company and the right company for the person. When you’re early stage, when to hire is when you don’t have any time left. You have to be pulled into it to actually hire somebody. When you are starting to hire a reverse engineer, the ideal state of your company in 18 months, figure out where you want to be and who you need to get there. Expensive mistake is to hire somebody with a Rolodex. If you don’t know what it is, Google it, but it’s a thing on your desk where all the numbers and names are in there. And with a big CV, in the end, that’s not going to work out. Ai is changing the functions of go-to-market engineer. It has been a hype. It’s a bit of a rapper for a lot of functions out there. But in the end, you need to find somebody who can enable AI in their function. Test the competency of leveraging AI. Find people who have been able to measure the outcomes of them leveraging AI.

[00:35:15.520] – Joran

And in the end, with AI, you can do more with less people. But it doesn’t mean you have to actually hire less. If you’re looking to go from EU to US, there’s going to be many hurdles and many mistakes you’ll probably make along the way. But you need to commit, go into the burn the boat strategy. So don’t have a backup plan. There’s no way back. And if you take it one step back, you need to be pulled into the YES as well. So get your first customers yourself. As a founder yourself, sell yourself. And then once you’re ready, build a full expansion strategy. Spend the time in the market yourself. Don’t hire in 20 year SDR and hope it will work. Remember, US people are going to be more expensive, a lot more expensive, so double the budget maybe, or as you mentioned, increase the budget plus 20 %. And then Remember, culture will be different. Founders who move to the US will be more successful. If you are doing PLG, self-serve product, it could be more easily to work your way into the US. For the future, prepare your sofa change because change is going to happen in a lot of areas.

[00:36:16.360] – Joran

Zero to 10K MRR, you need to have personal commitment. No one is going to care. Find a network of like-minded people and discuss your challenges. 10k to 1 million, higher ahead and higher right. Get help on hiring, hire where you want to go and hire on the skills for that. The favorite quote of the day, If you don’t have a seat on the table, you are going to be on the menu. If people want to get in contact with you, Chris, what would be the best way to-LinkedIn is the messy channel, but you could find me under Christopher Danon at Captivate on LinkedIn, or you can go to captivat talent.

[00:36:49.560] – Christopher Gannon

Com and find us there, and we’ll make sure we leave you with all those artifacts that we talked about.

[00:36:54.110] – Joran

Nice. Cool. We’re definitely going to add them in the show notes. I would definitely recommend people talk to Chris because Next to having a lot of knowledge, it’s always fun conversations as well. So thank you for coming on.

[00:37:05.260] – Christopher Gannon

Thank you so much.

[00:37:06.520] – Joran

Thank you for watching this show of the Grow Your B2B SaaS podcast. You made it till the end, so I think we can assume you like this content. If you did, give us a thumbs up, subscribe to the channel. If you like this content, feel free to reach out if you want to sponsor the show. If you have a specific guest in mind, if you have a specific topic you want us to cover, reach out to me on LinkedIn. More than happy to take a look at it. If you want to more about Reditus, feel free to reach out as well. But for now, have a great day and good luck growing your B2B SaaS.