S4E19 – Go To Market learnings from B2B SaaS Trumpet With Rory Sadler

Go To Market learnings from B2B SaaS Trumpet.

In this episode of the Grow Your B2B SaaS podcast, Host Joran sits down with Rory Sadler, the co-founder and CEO of Trumpet, a dynamic SaaS platform designed to streamline the buying process for customers. Since its launch in December 2021, Trumpet has rapidly grown, attracting hundreds of customers and thousands of companies on its free plan. 

In this episode, Rory shares the origins of Trumpet, detailing how he and his co-founders identified a crucial gap in B2B SaaS sales and built a solution to address it. He also opens up about Trumpet’s funding journey, the challenges faced, and the lessons learned along the way. From embracing technology and AI to maintaining a strong customer focus and building a robust social media presence, Rory provides valuable insights for SaaS founders and entrepreneurs looking to navigate their own growth trajectories.

How Trumpet Started

Rory recounts how Trumpet was born in summer 2021. He and his co-founders, Nick and Andrew, saw a common issue in B2B SaaS sales from their time at Hotjar and elsewhere. They wanted a centralized platform for sharing crucial info with buyers, which led to Trumpet’s creation. After talking to over 200 sales leaders and buyers, they were confident in their solution and moved forward.

Trumpet’s Funding Model and Growth Strategies

Rory talks about Trumpet’s funding journey. They raised £1.6 million in a pre-seed round in April 2022 and $6.35 million in July 2022 from investors like Albion VC and Lightbird. With around 30 employees, Trumpet focuses on providing exceptional service to all customers, big and small. Rory highlights their commitment to a close-knit team and standout customer experience.

The Importance of Focusing on Customers in Marketing

Trumpet’s core value is deep customer focus. Rory explains how they go above and beyond for their customers, aiming to provide outstanding service and encourage referrals. They also experiment with various marketing channels and partnerships to drive growth. Rory believes in starting with small-scale efforts, building strong customer relationships, and offering personal support.

Challenges and Lessons

Rory shares the tough lessons Trumpet has learned, including dealing with burnout and the need for a work-life balance. They faced challenges like deciding whether to build or buy parts of their product, which led to higher costs and delays. These experiences taught them to carefully evaluate when to develop in-house solutions versus using existing ones.

How Trumpet Uses AI and Tech

Trumpet leverages AI and tech to boost efficiency. Rory talks about using GitHub Copilot for development and tools like v0.dev for design. On the sales side, AI tools like Plexity enhance research and analysis, making prospecting faster and more effective.

Future Plans for Trumpet in 2024 and Beyond

Looking ahead, Trumpet plans to keep delivering a top-notch customer experience. They want to be more present with customers, offer face-to-face support, and ensure smooth onboarding. Rory stresses the need to focus on conversations that align with their target customer profile and continue their Product-Led Growth (PLG) approach while supporting smaller customers.

The importance of Building a Social Media Presence

Rory discusses the impact of investing in social media, especially LinkedIn. By consistently sharing valuable content and engaging with the sales community, Trumpet has built trust and attracted investors, partners, and customers. Rory advises other founders to use free resources and create helpful content to build a strong social presence.

Why Creating a Customer Advisory Board is Crucial

A key decision for Trumpet’s growth was forming a customer advisory board. This board, made up of industry leaders and potential dream customers, offers valuable feedback and insights. It helps Trumpet design a product that meets large enterprises’ needs and prepares them for future growth. Rory emphasizes the importance of choosing advisory board members with the right expertise and connections.

Advice for SaaS Founders

Rory gives several tips for SaaS founders. For those just starting, he suggests being scrappy, targeting the right customers, and using their network. For those scaling up, he recommends setting up a customer advisory board to gain insights and build relationships with industry leaders. Rory also advises balancing different go-to-market strategies and continuously experimenting to find what works best.

This episode provides valuable insights into Trumpet’s journey, highlighting the importance of customer focus, technology use, and relationship-building for growth. Rory’s experiences offer useful lessons for SaaS founders on their own growth paths.

Key Timecodes

• (00:00) – Introduction and Focus on Internal Success
• (00:50) – Guest Introduction
• (01:22) – Company Background and Revenue
• (02:52) – Product and Employee Overview
• (04:09) – Rory’s Entrepreneurial Journey
• (06:27) – Motivations and Company Vision
• (07:28) – Challenges and Personal Hardships
• (13:05) – Lessons for Founders
• (17:06) – The effective Growth Strategies
• (22:32) – Critical Decisions and Community Engagement
• (28:23) – Use of AI and Future Plans
• (34:07) – Advice for SaaS founders

Transcription

[00:00:00.000] – Rory Sadler

Focus internally on what’s working for you. Looking at your current customers, how do we find more of the same of them? How do we help our current customers get even more value from the product? How do we get them to the point where they have so much value from the product? They want to organically tell their network about it. That’s the obsession that you should have. As a startup, I think everything is against you. You’re not meant to succeed, you’re not meant to grow. No one’s heard of you. There’s no trust in you. Their friends aren’t using you. All of these things. So you’ve got to take advantage to the resources out there that are free because you don’t have all the investment to spend on digital ads and big marketing events and everything like that. If you’re going to invest the next 5, 10, whatever years of your life in all those hours and weekends and missing friends, birthdays, all this stuff, if you’re going to completely sacrifice all of that, you need to do it for a reason.

[00:00:50.540] – Joran

In today’s episode, my guest is Rory Sadler. Rory is the co founder and CEO of Trumpet, a SaaS solution which makes it easier for your buyers to buy. Before Trumpet, Rory started this career as a business development executive and fulfilled other roles like Account Executive, Head of Strategy, Sales Lead within SaaS companies of the like of Hotjar and Lerner Blee, and many others. At the moment, next to Trumpet, he’s also involved in multiple communities like RevOps, Co-up, Sales Enablement, Collective, and Pavillion. Let’s just dive right in. Welcome to the show, Rory.

[00:01:22.200] – Rory Sadler

It’s awesome to be here. I appreciate you. You’re having me on.

[00:01:25.040] – Joran

Nice. Let’s just get right started with the get to know you and Trumpet. Let’s start When did you start at Trumpet?

[00:01:33.160] – Rory Sadler

December 2021. The sick. Yeah, it’s the day of incorporation.

[00:01:38.220] – Joran

Is it the moment you actually started building or is that the moment of corporation and things happened already before?

[00:01:44.030] – Rory Sadler

Yeah, that’s where I got formal, it was the summer of 2021, where we were ideating and validating before taking the leap to spend the next 10 plus years building a generational company.

[00:01:55.740] – Joran

Can you share anything regarding revenue numbers? Where are you guys right now?

[00:02:00.880] – Rory Sadler

Yeah. Unfortunately, we’re not able to fully disclose due to investor pieces, but we’ve got several hundred customers continuing to grow. We do have a PLG motion, so I think there’s about 5,000 plus companies on our free plan, nicely converting one by one. But yeah, in a good position so far.

[00:02:17.920] – Joran

Yeah. You mentioned funding. Can you tell a little bit about that? How much? How many rounds?

[00:02:22.560] – Rory Sadler

Yeah. We’ve done two rounds to date. One was in April 2022. That was our pre-seed round. We did 1. 6 million I always remember that one in pounds, but our latest one is for some reason in dollars. We’ve just, as of July time, closed 6. 35 million dollars. That was backed by Albion VC in the UK and also continued support from Lightbird, who I’d recommend everyone’s speaking to, as well as Adam Kara, triple point Hatch. So yeah, some great European investors that we’ve got behind us.

[00:02:52.500] – Joran

If you look at your revenue, is there any separation between service and product revenue?

[00:02:57.460] – Rory Sadler

Not really. I’d say it’s like 98% product. We are starting to introduce more service. It’s an approach that makes sense for us as a business just due to the impact and the versatility of the product and the size of businesses that we work with. But I think in the early days, we not had it as too much of a friction point. In the world of sales, onboarding and account management is always a discount lever. So, yeah, we’re growing up. And I think it’s acknowledging actually the true value that we do deliver from the services side of the business.

[00:03:26.980] – Joran

Yeah. How many employees do you guys have right now.

[00:03:31.020] – Rory Sadler

Yeah, very proud of every single one of them. So still early days, that close-knit team. Everyone knows everyone. These are the most exciting days where you’re all in the trenches together. But yeah, we’ve got quite a few rolls out at the moment. So we’ll be going to about 30 soon.

[00:03:44.120] – Joran

Nice. In one sentence, what does Trumpet do?

[00:03:47.080] – Rory Sadler

Yeah. We’re helping revenue teams centralize their buying journey, increase their sales velocity with collaborative workspaces and digital sales rooms. It’s pretty much a one-link journey from that very first right through to onboarding and beyond. And it’s all about increasing collaboration externally. So we work with sales, CS, account management, partnerships. It’s pretty cool to see.

[00:04:09.600] – Joran

Let’s get to know you a little bit as well. Is this your first startup?

[00:04:13.360] – Rory Sadler

I’d say yes, with a pinch of a caveat. I think as an aspirant for many years, there was always like side hustles at university, running an events company, a couple of other things. And I had exposure to the world of investment-backed startups and then SaaS. When I was at university, studied entrepreneurship, if you can believe they actually have a subject on it, which seems nuts. But the main focus of it was take an idea to MVP. And I managed to do that. It was in the pharma tech space. I took the idea to MVP I had a health tech founder of a Series D company as a mentor. It was all progressing really well, working with the NHS, the UK Health Minister. It was all looking strong. And I was then offered ancient investment when I did the final pitch at university, but decided to turn it down. I wasn’t ready to build. I didn’t have a proper CTO. If I’m really honest, I didn’t really want to be in the world of pharma. From that two-year exposure to it, I just saw all of the regulation, the policy, and just how difficult it would be.

[00:05:14.040] – Rory Sadler

Many years later, I’ve now seen that idea being executed, which is great because I felt like at the time it was solving a problem, but I just didn’t have that passion behind it. I think that’s very important. So dabbled with the world of SaaS early on, and many years later, very fortunate now to be building. But yeah, I’m glad I did. Waited building network and the battle scars of being in and amongst startups and things like that.

[00:05:36.160] – Joran

You mentioned already you started a lot of side hustles in university. You even studied entrepreneurship. Have you always wanted to be an entrepreneur then?

[00:05:44.200] – Rory Sadler

Yeah, from a very young age, it was always the dream. Not necessarily for money or anything like that. I think it’s just to create a story, put your name to something, be proud of something, build a team, and go on a journey together. I don’t think there’s any experience that can make you as tired, but also be equally as rewarding. There’s all these different stages of growth, those challenges that you overcome as a team together. And I’d seen that within network, within some family, TV, Dragon’s Den in the UK, and all these different things. And I was just obsessed. I was that kid that was desperate to get a job as soon as I could. I wanted to grow up faster than the other kid. So I was just always drawn to the world of business. Never look back.

[00:06:27.510] – Joran

You talked about your young days as a kid. May I ask how old are you right now?

[00:06:32.180] – Rory Sadler

I am 30.

[00:06:33.140] – Joran

Do you have an end goal defined with Trumpet?

[00:06:35.470] – Rory Sadler

I’d say no. The reason being is, I think as soon as we started ideating, we were, as any founder, incredibly excited by the idea. We then started validating it and speaking to people in the world before going and building and seeing their excitement and their willingness to invest. And then we’re almost three years into the journey now. We just don’t want to stop. We know that the potential ahead is huge. If you just keep being obsessed with working closely with your customers, success in some shape or form will happen at some point, but it’s not really our focus. If you just continue building a best-in-class product, a best-in-class team, and working with incredible customers, actioning their feedback. Suddenly, you blink in, it’s 10 years in, and you’re just endlessly proud of what you’ve all achieved together. So yeah, there’s no defined strategy ahead. It’s just we’re learning what we’re doing right now. Let’s just keep at it.

[00:07:28.740] – Joran

I guess like something which also What keeps you motivated? You mentioned passion before, be proud of something. What keeps you motivated? What gets you up every day?

[00:07:38.300] – Rory Sadler

Yeah, I think the thing that gets me up every day is seeing the team’s passion. When I was at Hotjar, one of the things David, one of the founders there said, he didn’t expect everyone that joined Hotjar to live and breathe heatmaps. He said, They’re not the coolest thing in the world, but what I want to do is create a company where people love working with the team that they’re in, and they feel challenged, and they can feel that they can progress. They feel that they are helping their customers achieve something. And I think that honesty is people really respect it. At the end of the day, Trumpet, currently as a sales tech, if you’re going to categorize us by any means. And I love sales. I live and breathe it. I’m a sales nerd, but I know not everyone in the world loves sales. We’re trying to help change that perception, too. But I think it’s amazing to see the team that we have built and their passion for what we’re building and their advocacy for our customers and their care. Any time there’s customer feedback, big or small, it doesn’t matter who they are, it doesn’t matter if they’re an enterprise or a five-person, small early-stage startup.

[00:08:42.000] – Rory Sadler

There’s just equal care and attention to everyone, and I think that That’s pretty rewarding.

[00:08:46.110] – Joran

Nice. Let’s dive more into your journey. December 2021, Incorporated. Property ID came earlier already. How did you guys came up with the idea? What sparked it?

[00:08:57.600] – Rory Sadler

It’s an interesting one. I’d spent, after University, about seven years in B2B SaaS sales. I’d actually lived and breathed the problem that Trump was solving. At Hotjar, in particular, we were doing SMB, we were doing mid-market, doing enterprise all at once as one team. It was very messy. Usually, you have different teams for that. But we always believed in giving every customer a standout experience because that’s what Hotjar is about. That’s why people love them. They’re the brand that people resonate with. Whether we were doing a 5K deal or a 50 or 100K deal, it didn’t matter. Everyone should still have a great experience with us as a sales team because the face of the company in that experience. But we also had a lot of information to share with them. There’s privacy implications, security concerns. We had a deck, just demo recordings, the list went on. Being able to start centralizing that into Google Drive links and notion pages was where the initial idea for the Trump came about because I saw how receptive and grateful buyers were, and I realized how much it helped them be able to sell Hotjar internally. When the team started saying, Hey, can you build those for us?

[00:09:58.980] – Rory Sadler

Then something starts to click. Also my co-founders, nick and Andrew, we’d known each other for many years and came together with ideas, and they’d been thinking about something similar in the world of investment. When you go to raise from investors, there’s a lot of data sharing, a lot of data rooms, and it’s hard to stand out with all that noise. We put the two together and then went and spoke to about 200 sales leaders and people and about 200 end buyers to see, do people want this product and do people want to buy in this way? Yeah, it was pretty quick to head around, but we also They did a lot of market research, which I encourage everyone to do. I think a lot of founders or aspiring founders think that they need to have the next new big idea. I need to reinvent something. No one needs to have ever done this. For us, actually, there was a lot of validation in the market, for example, like DocSend, a way to share documents and get to where they’re being opened. There was a lot of incumbents and legacy players. For us, that was validation.

[00:10:49.360] – Rory Sadler

That gave us actually more confidence that this idea was the new, improved and better way of doing things, but lots more ahead as well.

[00:10:58.680] – Joran

It’s interesting because As you said, you lived and breathed the problem, so you knew that there was a problem, right? But still, you spoke to 200 leaders. You did market research to really figure out, is it just our company, but also are other people actually experiencing it?

[00:11:11.780] – Rory Sadler

Yeah, I think it’s a must because if you’re going to invest the next 5, 10, whatever years of your life and all those hours and weekends and missing friends, birthdays, all this stuff. If you’re going to completely sacrifice all of that, you need to do it for a reason. Not only that you’re passionate about, that resonates with other people. And before taking that leap, it’s not too much of an investment whilst you’re working another job to put in those extra hours and then validate that.

[00:11:37.120] – Joran

Yeah. At the moment, you guys said 5,000 companies using the free plan, a couple of hundreds using the paid plan. Did you know from the beginning it’s going to be such a success?

[00:11:48.480] – Rory Sadler

I think the research that we did speaking to all of those people gave us a lot of confidence. My cofounders are exited founders, so they built and sold a bootstrap SaaS company for near $30 million. It took them 9, 10 years to do that. So we knew that the journey wouldn’t be linear. It wouldn’t be straightforward. We didn’t necessarily know it would go as well as it has gone so far. I’m not saying it’s been easy. I’m not saying it’s been a complete success. It is still very early. I think in the grand scheme of the world right now, we appreciate what the team have accomplished given the really tough macro environment, and especially being a tool that helps companies sell more, quicker, and improve their sales efficiency and velocity. We use it ourselves, as you can imagine. It doesn’t mean that we’re immune from everything that’s happening out there, companies shrinking budgets and laying off teams and consolidating tech and all of this stuff. So yeah, I think from that we’ve had hard lessons learned, but we’ve just had to be ruthless and focus and work on the things that really matter and drive growth forward.

[00:12:51.180] – Joran

It’s a nice bridge into the next question. So you mentioned hard lesson learned. I think every founder hits rock bottom. One day, I guess maybe even before your journey at Trumpet, did you had a rock bottom moment yourself, either financially or personally, and how did you overcome that?

[00:13:05.830] – Rory Sadler

I’m very much a person who… I’m a very positive person. It’s hard to knock me down. I think build a tough skin many years in sales teaches you that, which is great for this journey. But I think with friends, family, work, I try not to let anything defeat me or put my hand up and say I’m not okay. And there was a point where I had a lot going on, personally. Financially, it was not in a good position. It was early days at Trumpet as well. And we were building the team, we were hiring, we just clicked go on the commercial driving revenue when you’ve got investors. Then once the revenue is going, there’s expectation. And all of these things together, it led to burnout. I hadn’t invested in myself properly, doing the things that I love, playing football. Not that I’m any good, but just to be able to take that stress out, being more present in my relationship with my now wife, and being more communicative with those around me, like when I need help and I can’t always take everything on. I think it’s very easy as founders to feel guilty when you’re not working, which you will appreciate.

[00:14:05.870] – Rory Sadler

Every waking moment, there’s always an email to reply to, there’s always a customer to serve. There’s always product feedback to action. And I think I’m glad it happened that early on because now it’s the understanding that it’s okay sometimes to have a day off or to take a small break and not have to work in that evening and just go and enjoy a meal with your friends and things like that. So yeah, just taking on too much at once in a very short period was pretty brutal.

[00:14:35.360] – Joran

Yeah. If you would, I guess, because a lot of SaaS founders are listening, right? I guess if you can rephrase it into advice for others, what would you tell them right now? What should they be doing or shouldn’t they be doing?

[00:14:46.570] – Rory Sadler

I think some sports, whether it’s yoga, pilates, football running, you’ve got to have some outlet that takes your mind off work fully, where you completely detach. I think that’s been really important for me is a time in the week, a couple of times where you just don’t think about work because we’re always thinking about it. And with that as well, it’s not feeling guilty when you’re not doing work. I did, especially at any point. I felt like I needed to be doing things seven days a week. Actually, you realize things don’t come down, crashing and burning and things can… That to-do list never, ever stops growing. You can never get it down to zero. Embrace that and know it’s okay.

[00:15:26.320] – Joran

Nice. I think for me, personally, ball sports, I I’ve always been a ball sport guy, so played football 11 to 11 until last year, and now I’m playing pedal. There’s no way you can think of work while playing a game like that. I would definitely recommend it. When we talk about challenging periods, you guys are now 22 team members, so have been growing good. I can imagine there’s a lot of challenging periods. You already hinted a little bit to it. What has been the most challenging period for you? Has it been the burnout period or has there been other moments which which have been super challenging for you?

[00:16:02.840] – Rory Sadler

Yeah, I think that that burnout piece was more like a personal thing. Most companies will go through this unless you’re from day one setting out to build a company that works the SMB space. But for us, it was that maturity, that stepping up of we work with lots of small customers and introducing those next-tier plans and introducing more customer success and deeper onboarding and training. It happens like overnight, you get those larger customers being able to serve them properly, having to go to getting your security certification ISO SOC 2. All of that can happen very fast. It can be a lot for the whole team, that progression up market. But at the same time, you’re not just dealing with that internally. It’s the external expectation of up and mid-market enterprise-sized businesses. They don’t want to have a buggy solution. They don’t want to mess around with a startup. They are investing in a piece of software because they are a global company and they need it to deliver the results that they promise. Sometimes you have these shifts, these moments where you go from being one company to another, almost, and it can happen very fast.

[00:17:05.500] – Rory Sadler

Pretty much overnight, one new customer can do that in the early days, and it’s ensuring that everyone’s able to adapt to that change because it can hit you quicker than you expect.

[00:17:14.260] – Joran

Because a lot of things will happen when you’re going to go up market, as you mentioned. You go from a chaotic startup, probably to a really organized one because you have to meet all the requirements of the certifications, of course. Are you struggling to find people and companies which have access to your ideal customer profile? At Reditus, we just launched a second site of the marketplace, which allows you to search, filter, and contact B2B SaaS affiliates which have access to the audience you’re looking for. We do this by leveraging first-party data sources. Want to learn more? Go to getReditus. Com. Let’s talk about positive things. So what has been some things you’ve done to grow Trumpet where it is today?

[00:17:52.600] – Rory Sadler

In terms of GTM, the last five years or so, we were getting to that point of SaaS just flying off the shelf, and everyone was like, put, just do more of the same. And here’s the playbook and go and execute, because all of these companies have followed that playbook. I think we’re in a climate where buying behavior has changed. There is no budget holder anymore. It is a committee, there’s multiple buyers, and that’s even at SMB. The thresholds for software approvals have disappeared. It’s all now with the CFO and the team around them. So we’re in a very strange climate. There’s a lot happening politically in the world as well. I think there are certain companies that you see, they’ve just nailed PMF and their product has just hit home with a real deep pain across so many businesses, and they just take off. Sometimes it’s a timing thing, sometimes it’s execution. But I think for the most part, they’re few and far between. Everyone sees these shining stories and things, Oh, why is that not us? But I think in the most part, seeing everything that’s shared out there on LinkedIn and all these startup playbooks, and here’s this company that went to 100 billion in three years, whatever it might be, it’s easy to get distracted.

[00:18:58.730] – Rory Sadler

I think the first thing is just focus. Focus internally on what’s working for you. Looking at your current customers, how do we find more of the same with them? How do we help our current customers get even more value from the product? How do we get them to the point where they have so much value from the product? They want to organically tell their network about it. That’s the obsession that you should have. So I’d say as a go-to-market strategy, that’s been integral for us is living and breathing a value that we’re very proud of and take very seriously, like that true customer obsession. White glove service going the extra mile for them and making them feel like they’ve changed the game for their team by working with us. So that’s one part. The other thing is, when I’m speaking about all of these, here’s this playbook, here’s what everyone else has done, these years of seeing the repeatable processes happening, I think we’re now in a climate where that just doesn’t work. You need to be trying different things all the time. We’re a mess internally. We are doing probably way too much than we should be.

[00:19:56.530] – Rory Sadler

Everyone’s wearing way too many hats. We’re trying far too many different channels and partnership strategies, but it’s because it’s really hard. We’ve made a lot of noise from the outside. We’re growing pretty well, but we’ve got to hustle. This is really being in the trenches. And I think trying to rely on one channel and double down on it, there’s high risk with that in this environment. So I would encourage people to, as Paul Graham said, do the things that don’t scale. For us, we’re being in person as much as possible, being able to meet those execs, those decision makers, and being on-site training. We would love to be pure PLG, and the software is completely hands-off, but it’s just not the case. We’re trying to show our investment to our early adopters and our customers by being face-to-face as much as possible.

[00:20:43.620] – Joran

I’m curious, how does Does it work well with the VCs you guys have on board? Because they often want to have predictable scalability or they want to know exactly what you’re going to do. You mentioned true customer obsession, which I love, but then it’s hard to say we’re going to generate X amount of revenue when we keep doing that. In person events, it’s always a bit harder to justify or to make it scalable. How do you work that out? Doing these things and having a VC on board as well?

[00:21:12.020] – Rory Sadler

We’re very upfront with that conversation, and I think it’s everyone just being quite candid. That zero to one journey, it’s scrappy. It’s like any customer, anyhow, there’s different contract terms and different discounts. You can’t really have it repeatable because I personally think there’s nothing more valuable than having someone actually using your product daily than whether it’s a five, a 10, or a 20K contract. And that sounds stupid, and we should all be very revenue-focused, and I’m not saying we’re not. But sometimes avoiding friction to get someone winning with your product is going to create an advocate. And as long as you’re building the company together with them by listening to their feedback, that investment in them and that flexibility, it will come back to reward you for sure in the future. That’s here. It’s one journey. It’s scrappy. It’s any shape or how the one to 10, the one to five, whatever it might be, that’s where you start to think about more repeatability and process and being able to scan up the team and be able to reflect what has worked and look at our best customers, the ones who are using it the most.

[00:22:07.660] – Rory Sadler

Where do we find them? How do we engage with them? I think it’s unfair for DCs to expect a perfected playbook in the first two, three years. Everyone wants to move away from that as soon as possible because it doesn’t become very manageable either.

[00:22:21.840] – Joran

Nice. I guess if you look past at your journey, did you guys make any critical decisions? Hey, if we haven’t done XYZ, we wouldn’t be here right now.

[00:22:32.470] – Rory Sadler

I would say our investment in social. So if I split our journey, year one was building the product, the beta. We were doing research, we were building our content strategy, we were immersing ourselves in the world of sales and revenue and things like that. And then year two, we started to commercialize. Year three, we started to move our market. Typical growth journey, I think. But throughout, even from day one, we announced Trumpet to the World, but we didn’t say exactly what it was. We didn’t give much away, what it looked like. So we started to create FOMO, and we started to be very present in the sales community, building this waitlist was actually something that was quite successful for us. But all of that came down to leveraging LinkedIn and social channels because it was free. As a startup, I think everything is against you. You’re not meant to succeed, you’re not meant to grow, no one’s heard of you, there’s no trust in you, their friends aren’t using you, all of these things. So you’ve got to take advantage of the resources out there that are free because you don’t have all the investment to spend on digital ads and big marketing events and everything like that.

[00:23:30.840] – Rory Sadler

So for us, posting daily, religiously on socials, value-added content. We were sharing best practice in terms of sales or building startups and things like that, both me and one of my cofounders, and then the team started doing it as well. So as a company, it’s quite unique. We know that our ICP and our buyers live on LinkedIn in particular, but we wanted to start investing in that world and that community by creating content for them. I think that investment from the very early days has now compounded. So when people think of our space, they think of Trumpet. And they also have trust in us because they know that we don’t just push the product and say we’re the best thing ever. We’ve been sharing content that can help their team grow and help their team sell and help their team renew their customers, all these different things. Yeah, I cannot recommend enough the power of building, I guess, engaging in the world of socials.

[00:24:22.620] – Joran

Yeah, because I just checked your LinkedIn profile again, 32,000 followers. So you’ve been going at it nicely. And in the intro, we mentioned you’re part of the RevOps co-up community, sales and name it collective and pavilion. So are those the things that summarize it? Like really heavy on LinkedIn, 30K plus these communities.

[00:24:41.520] – Rory Sadler

I think I’ve tried not to pay too much attention to the follow-up account or anything like that. I think if you become ego-stroking, how many likes did I get? How many comments did I get? And what posted well and what didn’t? I think for me, every single day, I’m now on the routine. I’ve not posted on a day since starting to jump it, and It was just coming into the office first thing. It’s the most messy note list in the world. I just have ideas on what I’m at and about, and I jot down the idea. I take the idea each morning, and then I’ll just flesh it out first or after it, go make a coffee, come back, finalize it, post it. If it does well, great. If it doesn’t matter. I’m not posting on there to build a following or to get lots of likes is to just share things that have worked for me, that I’m seeing, that I’m learning. And if it does well, great. Unfortunately, it has compounded and it has led to us attracting investors and building partnerships and getting customers. It does work. But equally, I would be able to do that without engaging and meeting and learning from other brilliant leaders and thought leaders that I’ve followed and I’m inspired by on LinkedIn.

[00:25:43.300] – Rory Sadler

And that also comes from the communities. I think the power of community is underappreciated. I think there is an assumption you become a member of Pavilion and you just start getting customers. You start getting results from it. It’s not the case. You get out where you put it. If you go to the events and you’re active the Slack channels and you engage with the posts and you recommend your friends and you become really part of it, that’s when it starts to yield results, whatever those results are. But yeah, I think people just see a Slack channel, lots of channels within that group, that community, and they don’t know where to start and they lose interest and pays out. So it just depends what you want. If you’re really passionate about that space, then they’re invaluable for sure.

[00:26:23.300] – Joran

Yeah, because these things have been working real nice, and I guess with all success, failures also are part of it, right? Can we talk about one of your biggest failures and how did you overcome that?

[00:26:34.780] – Rory Sadler

Yeah. The product team won’t mind me sharing this because it was something that we were all quite honest about afterwards when you do a bit of a reflection on a certain launch. I think it’s the buy versus build argument. We’re very fortunate. Building in SaaS right now is arguably, and it’s only going to ever continue to be easier than ever because tech and building is becoming more and more commoditized and more accessible and faster. And let’s not even get onto AI because we’ll talk about that for hours. But there’s still always argument of buying versus building. There’s certain parts of a product that you can either integrate and leverage an SDK, for example, or you can be like, I’m going to go ahead and build it myself. And I think we made the wrong decision with one of the parts of the product to build it ourselves. And what would have probably taken 2-4 weeks with an SDK investment, and it wouldn’t have been much, several thousand dollars, we decided to build it ourselves and it ended up being a three, four month project costing us a lot more. You start to assess the resources, the time, the team, the And today, what we’re left with is still not what we wanted back then.

[00:27:34.640] – Rory Sadler

It was a great learning. You have to have these mistakes. It’s just not a perfect journey. So we’re actually super grateful that we had that. That thing go wrong because now we are able to quite clearly assess when we got a new project coming up, what exists in the world already that we can start to leverage and how quickly can we get started with that versus we can build from scratch. Buy versus build, forever the biggest debate in product teams within SaaS.

[00:28:01.420] – Joran

Nice. But it’s a mirror you can hold in a meeting. Are we going to do the exact same thing which we did before or are we going to learn from it, I guess?

[00:28:10.040] – Rory Sadler

Yeah, for sure.

[00:28:11.720] – Joran

You did mention it a little bit. You can talk about it for hours. We’re going to talk about it for a couple of minutes. How do you guys leverage it internally? Talking about AI, machine learning, all the new technologies out there.

[00:28:23.420] – Rory Sadler

Yeah, I know the product team use GitHub Copilot. That’s helped increase their efficiency. I would recommend that to anyone. We use the v0. Dev, which is a great tool if you’ve not checked it out. For someone like I’m not a developer, but I’ve got lots of ideas and got this vision for Trumpet and sometimes being able to mock up a simple wireframe using it just through AI and prompts. For example, build me a dashboard that does X, Y, and Z, and then I can give it the prompts, it’s right on it. I can then share it with the team and say, I’ve got this idea for something that looks like this. We’ve now, fortunately, got a product design team who can help make it look A hundred times better. But it’s a nice, nimble, easy to use tool that just helps us work more efficiently and accelerate that scoping side of product development. So on the product side. Reporting goes without saying. My financial reporting metrics is just AI has been a game changer for that, a lot more automated and seamless. Interestingly on the go-to-market side, so for sales, AI has helped accelerate our research.

[00:29:23.490] – Rory Sadler

What would have taken 20 to 25 minutes per account before, it’s, I’d say less than a minute now to produce the same results. For us to… On the sales side, actually, I’d really recommend for plexity. It’s able to assess a lot more sources of content than OpenAI and ChatGPT. It’s able to look at someone’s LinkedIn profile, their website, and other blogs, and doing a lot more dig and deeping. I think it combines some results from like Claude and ChatGPT. I might be wrong there. But for me, that’s been great for researching, building all sorts throughout the sales cycle. We’re a company that embraces AI. I I think it’s going to become increasingly part of our infrastructure, and that’s excluding our own product as well.

[00:30:07.220] – Joran

Yeah. One final question before we dive into the closing questions. If you look at now 2024, you mentioned a lot of times already, times are changing, buying size is different. What are your plans for 2024? Maybe even going already to 2025. I don’t know if you plan that far. If you look at go-to-market, what are you guys going to do which you hope is going to make the difference?

[00:30:29.100] – Rory Sadler

Yeah. I think we’re going to continue doing things that don’t scale. For us, that means delivering a best-in-class, stand-out, white-glove customer experience. I don’t think for us, our software is all about asynchronous collaboration, and it’s very easy to use, but we still want to be as close to our customers as possible. We’re going to actually be doing more of that rather than trying to become a very lean CS team. I think, fortunately, there’s been a resurgence of CS. I think for the last few years, it was like, How do you have really small headcount in CS? And now everyone’s like, Oh, wait, we need NRL. Actually, renewal is really important, all this stuff. So we’ve always believed in that. In fact, our first go-to-market hire was our head of CS. So from day one, we’ve invested in the experience from start to finish, including support. So we’ll be doing more of that. I think a big piece which What small companies need to do and sales people need to understand the value of is qualifying out conversations. In sales, it’s very easy to get happier. Someone says your product is cool and they would love using it, but it doesn’t mean that the business needs it.

[00:31:30.560] – Rory Sadler

There’s two very different things. I think for us, it’s being able to focus more and work with the right opportunities and customers and prospects who have a real pain that we’re going to be able to solve, and not just people that have seen us on LinkedIn and think it’s cool and they want to check us out. I think qualification, the reason being is it improves efficiency and a sales velocity and it improves your metrics, but it also alleviates time on the team. It’s easy to just have endless calls and demos all day, but then if they’re not all progressing, then let’s qualify out sooner. It’s hard in this market just to get a call with someone. I think a lot of people are like, Yeah, but I can win them round. It’s a tough skill to learn in sales. It’s qualifying out. When is it an opportunity? Really an opportunity.

[00:32:11.020] – Joran

You also mentioned you guys are going for PLG or at least trying. It’s not always working as you want, especially early days. How are you going to combine it? Like, focusing more on your ICP, but also keeping that PLG approach because you can’t always control who’s going to sign up or book a demo.

[00:32:27.040] – Rory Sadler

Yeah. Plg is not an overnight I think you see all those graphs on LinkedIn, on Figma, and ClickUp, and all these companies, like when did they hit their inflection point? Some of them took many years. And PRG doesn’t necessarily mean you have a free plan, people sign up. There’s so much to it as you will appreciate. For us, we’re big believers in buyer enablement, making it easy for your buyers to buy. So for us, we don’t want to gate the product. We’re proud of the product. We want people to be able to try before they buy and explore it and investigate, and whether it’s just one colleague using it or something like that. The way that we think about it is it’s always there to also serve the customers that are pretty small and we’re maybe not able to serve this because of the small size of the team. So we always want to be able to support the small guys. That’s where we came from. Every customer deserves a seamless experience. They shouldn’t be gated from getting access to the product. So we want to enable that. It enables us as well as sellers to then leverage product-led sales motion.

[00:33:20.220] – Rory Sadler

We’re getting insights when someone from a certain size company signs up and they invite their team and they start looking regularly and they hit the cap. And then we can start to support them with that journey. Is this an evaluation you to progress and discuss with the right people internally because you hit a cap? So yeah, I think it enables for signal-based product-led sales. Yeah, we’re pretty much doing every motion, PLG, PLS, traditional top-down sales. That’s what I said at the start. It’s doing everything.

[00:33:45.460] – Joran

Exactly. I think as you mentioned, you do so much, so many experiments at the same time. It’s a bit chaotic, but I guess that’s the startup life.

[00:33:52.840] – Rory Sadler

Yeah, that’s what we signed up for.

[00:33:54.520] – Joran

Exactly. Let’s dive into the closing questions. So these are going to be revenue-related We did. What advice would you give another SaaS founder who’s just starting out and trying to grow from 0 to 10K monthly per current revenue?

[00:34:07.280] – Rory Sadler

I’d say embrace the scrappiness, I think. Don’t get too distracted with big logos really early on. If you know you’re building a product for enterprise from day one, that’s different. If you’re still figuring that out, enterprise is all the shiny big budget, but it’s going to be more distracting. It’s going to take longer than you ever think because you don’t have MFA, you don’t have missions, you don’t have SOC 2, you don’t have custom, whatever it might be or a certain integration. There are so many requirements that founders miss when they start. They have a conversation with someone, I’m like, I’m speaking to so and so at MONGODB or someone at Salesforce. Do you really understand what it’s going to take for that organization to back a startup where there’s maybe 6, 10 of you and you’ve been going just over a year? It’s probably not going to happen. We were naive. In the early days, we had a few people set up from big logos. We got distracted and we thought, Oh, we can get them on. But actually, it’s being aware of where you really are and what customers can you actually serve and focusing on them.

[00:35:06.880] – Rory Sadler

And then there’s this concept of the Berlin hand principle where you really lean into your network, whether it’s someone that can do great photography or it’s someone who’s got a podcast you do at their co-working space. Lean into all these people, be scrappy with the resources you have around you. And through that, one, you’re then increasing your network. But two, you’re not putting all the pressure on doing everything yourself internally. I think you feel like you need to do that. You have to do everything yourself. But yeah, there’s no golden ticket. Here’s the one thing to do. I just say, embrace the scrappiness. Actually, I go back to what I said earlier. Getting customers using your product is more valuable than the actual exact dollar amount.

[00:35:45.660] – Joran

Exactly. And probably also then the actual logos on your site. You need to have people using the product. Nice. Let’s assume we pass 10K MRR and we’re going to make a huge jump towards 10 million ARR. What advice would you give SaaS founders here?

[00:36:00.620] – Rory Sadler

I’d explore the concept of a customer advisory board. These don’t necessarily need to be customers of your product today, but they can also be customers that you would dream of having one day. So we’ve built one. So we have one of the EVPs at HubSpot. We’ve got CROs from Cumultor Calendly. We’ve got revenue enablement leaders for the likes of Databricks and GOM. These are dream logos and customers, but they’re also experts in their space and their field and their domain. And we’re working with them to build Trumpet together. So how do we get Trump to become a $100 million company? How do we sell to $100 million ARR company? What would you want to see? What are the things that are missing? What are the capabilities that you guys are thinking in the next five years? Because when they’ve got thousands of sellers, for example, we sell people globally. We’re aware we don’t necessarily know that world right now today. So how can we be aware of it? So in 2-3 years time, when we’re ready to engage with that world, we’ve had the support of being able to build that in mind. And those people have incredible networks.

[00:37:00.000] – Rory Sadler

They have incredible expertise and domain knowledge that you can just tap into. We’re fortunate to build the customer advice report that we’ve got. It is equity-based. It’s not necessarily how many you have. I think just making sure you do the due diligence on who they are and what value they’re going to bring is probably the key piece.

[00:37:18.700] – Joran

Nice. Love it. Let me try to summarize 40 minutes in, let’s say, two minutes. You started Trumpet like you lived and breathed a problem, but I guess that wasn’t enough. You also spoke to 200 leaders, did a lot of market research, and as you mentioned, doing proper research will give you the confidence going forward. Keep investing in yourself. Do things which can take your mind off work, and definitely don’t feel guilty when you’re not working as a SaaS founder. Moving up market means you will have a lot of challenges. You almost become a new company. Buy decisions have changed. You now have committees and always have to go through the CRO when the company gets bigger. Your GTM, a true customer obsession, and keep experimenting with many channels. In your case, maybe too many, but embrace the chaos. Don’t focus on scalability, repeatability too early. Do things that don’t scale. Don’t get distracted on the big logo. Stay scrappy and keep focusing on your ICP. Investing in providing content, building communities will compound, and it will only work when you’re being part of it. So you get what you give. Start a customer advisory board, find expert dream clients, and build your company together with them.

[00:38:27.410] – Joran

They will have networks, expertise, and great knowledge, and you can get them in by giving equity away. And that is a short summary. If people want to get in contact with you, Rory, what will be the best way to do this email?

[00:38:39.000] – Rory Sadler

So LinkedIn. I’m very active. I’m very present there. Linkedin’s inbox is not the best, as we all know. So if I I don’t think I’ve ignoring. Sometimes I just miss things.

[00:38:47.560] – Joran

Cool. Then we’re going to link both and make sure to follow up with Rory on LinkedIn if he doesn’t respond. For people listening, if you got to this far, please leave us a review on Spotify, Apple podcast or wherever you’re listening and make sure to fill out the poll we’re going to add to this podcast as well. Thanks again for coming on, Rory.

[00:39:05.680] – Rory Sadler

Pleasure. Thanks for having me. Great to chat.

[00:39:07.900] – 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 If you want to know more about Reditus, feel free to reach out as well. But for now, have a great day and good luck growing your B2B SaaS.