S4E2 – How Cybersmart grew to $5M ARR with $20M in funding With Jamie Akhtar

featured image

Jamie, CEO of Cybersmart, shares invaluable insights and strategies for B2B SaaS founders navigating the journey from startup to scale-up. From effective time management to fostering a supportive company culture, Jamie offers practical advice gleaned from his own experiences. Whether you’re striving to reach $10k in monthly recurring revenue or aiming for $10 million in ARR, this episode provides actionable tips to help you succeed in the competitive world of B2B SaaS.

Transitioning from a hands-on founder to a visionary leader requires a shift in focus towards strategic initiatives and personal growth. By stepping back from day-to-day operations and honing in on high-level goals and vision-setting, founders can steer their companies towards sustainable success. Embracing change, fostering a robust company culture, and focusing on personal development are essential components for navigating the complexities of scaling a SaaS business. The evolution from being deeply involved in every aspect of the business to empowering the team and driving organizational success is a crucial phase in the founder’s journey.

Key takeaways

  1. Clarity with OKRs: Establishing clear objectives and key results (OKRs) provides direction for both individuals and teams, guiding them towards common goals.
  2. Time Management: Effective time blocking, supported by an excellent assistant or chief of staff, enhances productivity and ensures focus on tasks that matter most for a SaaS founder.
  3. Identifying Unique Contributions: As a founder, determining what tasks only you can do is crucial. Delegating other responsibilities allows for a more strategic focus on driving the company forward.
  4. The “Deep Zone”: Setting aside dedicated time, like a “deep zone” day, facilitates focused thinking and ideation, leading to more impactful outcomes.
  5. Embracing Creativity: Recognizing when you’re in a creative zone and aligning tasks accordingly optimizes productivity and idea generation.
  6. Value of Idea Banks: Recording ideas as they arise, then revisiting them during dedicated time blocks, helps prioritize and refine concepts effectively.
  7. Importance of Information Flow: Streamlining how information is communicated and decisions are made within teams enhances efficiency and fosters collaboration.
  8. Culture Investment: Overinvesting in company culture is key to attracting and retaining talent, driving change management, and maintaining a shared sense of purpose.
  9. Personal Focus: Founders must resist the temptation to be involved in every detail and instead focus on strategic planning and decision-making to propel the company forward.
  10. Perseverance: Success in entrepreneurship requires resilience and determination. Embracing setbacks as opportunities for growth and staying committed to the journey is paramount.

Key Timecodes

  • Jamie’s Background and Entrepreneurial Journey (00:37)
  • Goals and Motivation (01:46) 
  • Company Overview and Metrics (02:28) 
  • Funding and Investor Relationships (03:18) 
  • Product Market Fit and Customer Feedback (05:11)
  • Go-to-Market Strategy and Channel Partnerships (12:27)
  • Company Challenges and People Management (16:37)
  • Personal Development and Time Management (30:26)
  • Advice for SaaS Founders at Different Stages (35:41)
  • Jamie’s Advice on Leadership and Planning (39:38)
  • Encouragement for SaaS Founders (40:06)
  • Stay Quivered – Perseverance and Adaptability (40:57)


[00:00:00.320] – Joran

We’re doing another live episode here in Marrakesh. We’re gonna meet up with other SaaS founders for the Saastock founder membership Retreat. Quick reminder for season four, we’re gonna focus more on founder to founder learning. So really diving into the founder journey challenges, mistakes, things that went well, but also, I guess, the things that didn’t went well. So you can copy those or avoid the mistakes. My guest today is Jamie Akhtar. Jamie has multiple roles as a technical and commercial leader before starting Cybersmart. He is co founded Cybersmart in 2016 and is the CEO right now. It is nice to get a technical founder on this show. So welcome to the show, Jamie.

[00:00:37.740] – Jamie

Thank you.

[00:00:38.140] – Joran

We’re going to do a fire round, in a way. Was Cybersmart your first startup?

[00:00:42.240] – Jamie

It wasn’t actually, no. It was my first tech startup, though. So I’ve basically run my own business entire career, so I’ve never actually been employed by anyone. I think I am unemployable.

[00:00:54.470] – Joran

So have you always wanted to be an entrepreneur?

[00:00:56.640] – Jamie

Yes, for sure. I think it’s been something that I remember back in school, like selling Pokemon cards and doing whatever I could to pay my way to make a bit of pocket money. Back in the days, I actually did a masters in entrepreneurship. That’s an actual degree. Okay, it is a degree. So I studied entrepreneurship as well, mostly because I did business before that, and I was like, this isn’t. I don’t want to work for a corporate. I knew I didn’t want to work for a corporate. I knew I want to do my own thing.

[00:01:21.370] – Joran


[00:01:22.010] – Joran

And have you defined a goal with Cybersmart? Like, where do you want to take it?

[00:01:26.270] – Jamie

I’d say no. And I’ve never really sat down and done that, and that probably sounds really silly, like saying it out loud. I always really focus on, is this something I really enjoy? Is it something I can learn from? And is it something that’s going to have an impact in the world? Again, very cheesy, but I really love, for me, the joy comes from learning, developing, having impact.

[00:01:46.630] – Joran

And is that also the thing which keeps you motivated?

[00:01:49.430] – Jamie

I’d say to a large degree, yeah. I think constant challenge, constant obstacles, or things that you need to overcome. I think most entrepreneurs are like that. We enjoy that discomfort of not knowing something, not being able to do something, and actually getting over the hill, if you like. So that’s definitely a big motivator for me. I think the other big one is people. So seeing my team develop and grow, seeing our customers grow, when a customer is happy. It’s like one of the best feelings.

[00:02:16.630] – Joran

In the world, in my opinion, and real personal one. What is your age?

[00:02:21.290] – Jamie


[00:02:22.160] – Joran


[00:02:22.820] – Jamie


[00:02:23.520] – Joran


[00:02:23.960] – Joran

We’re going to dive into company because I guess we haven’t even discussed what cybersmart does. So what does it actually do?

[00:02:28.670] – Jamie

So Cybersmart is a platform for small businesses to better improve their cybersecurity. Our aim is to give them a connected, accessible platform that empowers them with complete cyber confidence. We mostly work with channel partners to get our product into those small businesses. So in our case, they’re mostly managed service providers.

[00:02:48.790] – Joran


[00:02:49.170] – Joran

We’re going to dive into that more. What is your current ARR?

[00:02:51.970] – Jamie

Right now we’re at 5 million.

[00:02:53.990] – Joran

Nice. And is it purely product revenue? Also services.

[00:02:57.400] – Jamie

It’s product led. So all of our core technology essentially allows them to understand their cyber risk. To get on top of that, we look at people, process and technology within a company basically goes from like zero to one cybersecurity and keeps them at one.

[00:03:12.030] – Joran


[00:03:12.630] – Joran

And how many employees do you currently have?

[00:03:14.810] – Jamie


[00:03:16.070] – Joran


[00:03:16.900] – Joran

And did you take any outside funding?

[00:03:18.910] – Jamie

We did a lot of. Many funding rounds at 20 million.

[00:03:23.300] – Joran

20 million. And how many funding rounds was that.

[00:03:25.800] – Jamie

Including all the bridges and everything? Probably about six or so. Okay.

[00:03:29.750] – Joran

And would you do differently next time? Because sometimes you hear people don’t want to go funding versus one state bootstrap. Would you do it exactly the same or different?

[00:03:36.930] – Jamie

I personally would. I think it’s a choice. I think it’s a decision, but I definitely would do the same. I think a lot of it is about the investors you bring on board. Almost every founder I speak to that hates their investors or regrets it is because of the people they brought on board, the decisions they took.

[00:03:54.450] – Joran

So I guess maybe then one dive deeper here, what have you done differently than them to get good VC’s in or good investors?

[00:04:02.730] – Jamie

Look, it as a two way process. Optimize for who’s going to help the business the most versus who’s got the best terms. Two way process. You’re interviewing them. You really want to know that you can work with these people, that you can. You’re going to spend a lot of time with them, probably more than like, your spouse, so you better enjoy that working relationship. And you both got to have the same goal. All parties need to have the same goal, otherwise it starts to create a lot of friction.

[00:04:26.680] – Joran


[00:04:27.430] – Joran

Maybe then even to come back on the first thing you said, you don’t have a goal to find. But in the end, the VC’s would probably want you to have a big goal in mind. We have a goal. Get bigger.

[00:04:37.450] – Jamie

In terms of this is something that’s crystal clear, we’re going to get to this or I’m going to do this, I’m going to retire and go and sit on a boat or something. I think it’s always about having a direction, travel. But we want to help customers, we want to protect all the world’s SME’s from cyber threats. Right. So that is a goal. But from my perspective, it’s not like I need the business to go from a to b and when it gets to b, then I’m going to be out.

[00:05:00.620] – Joran

Nice. Cool.

[00:05:02.280] – Joran

Now, I guess these are the real fire questions. Let’s just dive a bit deeper in a more flexible way. How did you come up with the idea of cybersmart?

[00:05:11.020] – Jamie

Cybersmart, I think like all the previous businesses were just talking to customers, listening to what the challenges was. I read a book recently recommend it called Kind Folks finish first and then talk about essentially the three ingredients. Right, of a good venture. The first is having, listening to the market, so understanding the customer need. The second is following your passion or something you enjoy, and then the third is your skillset. So I think looking at those three, like almost like a Venn diagram, right. You can’t just take two, you can’t just say, oh, it was a big problem and I really enjoy this problem space, but I have no idea what I’m doing. You’ve got to upskill very quickly, I think, where you can really excel and build something special is where those three things come together.

[00:05:52.970] – Joran


[00:05:53.380] – Joran

And that is what you did for yourself with Cybersmart.

[00:05:56.250] – Joran


[00:05:56.540] – Jamie

I love, I. I love cyber security. I think it’s a fascinating field. It’s so deep, it’s always changing, it’s always evolving. There is a massive need, like millions of business out there struggling with cyber risk and challenges. And my background’s in technology and cyber, so worked as a security professional doing pen tests and ISO audits and everything in between. So that’s really the three coming together. And that’s why I think, seven years on, I’ve still got the same passion and motivation and drive to make it bigger, make it better.

[00:06:24.660] – Joran

In the end, you’re in a market which keeps evolving, which keeps getting more important, I guess, nowadays, and bigger challenges to handle.

[00:06:31.820] – Jamie

100%. The Allianz publish a risk report every year. It’s not the most interesting read, but it is for people like me. Cybersecurity, ten years ago was number eight in that. And it was actually mixed with failure and other things around it. This year, it’s number one. And by a clear margin over that time period, it’s become way more important to society, to the world.

[00:06:54.810] – Joran


[00:06:55.570] – Joran

And I guess if we go to the journey of cybersmart. So now it sounds easy, right? You have good revenue, but I guess, like, getting product market fit as a cybersecurity tool, I can imagine that maybe is a bit more difficult than any other kind of tool. Like, how did you achieve product market fit?

[00:07:12.400] – Jamie

Yeah, well, product market fit, I think, is a bit of a. I love the term. It’s a liquid, not a solid, because it’s not something you ever really achieve. It has to adapt. I’m sure blockbuster had product market fit at one point, right? And now everyone watches Netflix, etcetera. I think that’s probably the first thing to understand. I think it’s too easy as founders to be like, oh, I got product market fit. I’ve not got product market fit. I think you can tell when you don’t have it, though, that’s for sure. Because nothing is working and you’re spending lots of money and lots of time, and it feels like it’s a tremendously uphill battle. And then there’s times when actually a lot of stuff falls into place. And the way we’ve found our way through that, like our playbook, if you like, was really listening to our customers. I think that’s probably most important thing. No matter what industry you’re in, no matter what you’re doing, spend as much time with your customers as you possibly can. And I think we’ll come on to how you balance that later. Because listening to them too much or without your vision is also a bad thing.

[00:08:09.950] – Jamie

I think the next thing is you need to like when stuff is working, double down on it, and also let go of stuff that isn’t working. We’ve often in the past, or I’ve been like, I can see this working, but it’s just not the right time or it’s not in the right market. And sometimes you need to pull back from those bets or take smaller bets in the future. So I think when you place a bet and it’s starting to pay off, then double down. And the last bit, I think, sell the product. I think a lot of founders, a lot of people I’ve seen in incubator mode, for stealth mode for so long, try and sell the product, put it in a customer’s deployment, try and get as much real life feedback as you can, because that’s where 100 people tell you the product’s great, 100 people tell you to buy it. But when you actually ask people to stamp up their cash and ask them if it’s delivering value, you really don’t.

[00:08:59.710] – Joran

I think, yeah, I think. And that’s the first thing you mentioned, right. Talk to your clients. So if you’re always in stealth, then you can’t talk to the client. So get it out there, have them start paying for it. So that’s the willingness to pay and then really see if they’re getting value out of it.

[00:09:13.630] – Jamie

Yeah. Even if you want to build, like a Freeman PlG motion, I think monetize early, ask people to pay early, even if it’s a fraction of what they will pay, with the intention that you’ll ask them at the end. So would you have paid ten times more for this? Because that’s what we’re looking at charging for it.

[00:09:31.120] – Joran


[00:09:31.960] – Joran

And I guess you mentioned it already a little bit. Talk to your clients, but not listen to them that much. As in, like, the roadmap, what are some of the key learnings you had getting this right for yourself?

[00:09:43.650] – Jamie

There’s a lot, and it’s a balance, I think, product vision, and I’m a technical founder, I’m very much obsessed with what the product can do and what it can be and product roadmap, etcetera, that’s one lens. And then you’ve got the customers and their problems today and the challenges they’ve got today in the way. So they solve those problems often not in line with what you’re proposing. So sometimes you can bring on the journey. So this is a better way of achieving your goals. If the gap’s too big, then there’s just. It’s like a chasm and you can’t really cross it. So you have to keep the product vision strategy in mind, but you also need to adapt that to customers. A lot of it comes down to timing, a lot of it comes down to the types of customers you work with. You often find in the earlier days. You’ve got early adopters that love trying new tech, and I’ll give you one set of feedback that is, yeah, keep going, keep innovating, keep building. Next thing, and then you’ll talk to your move into the early majority and they’re like, yeah, but Xtool has this feature, CSV exports or something.

[00:10:41.400] – Jamie

It’s actually a common request we get and we’re like, our platform is supposed to solve this problem. Like, why do you want a CSV export, and we resisted for a long time. And eventually you have to give the customer what they need want that fits in their workflow. So finding that balance is a real challenge.

[00:10:58.430] – Joran

Yeah, it’s interesting, even though you don’t need it, sometimes you have to deliver things, which I guess the customers request.

[00:11:04.840] – Jamie

Yeah. I’d say the worst situation, though, is you only listen to your customers and you lose sight of what you have set out to build or direction of travel. I sit worst, in my opinion. Sometimes it can be the right thing for the business. And if you’re a sales led organization, definitely that’s what you should be doing. You don’t want to become a company that is simply building stuff that customers need. You want to show them how they can improve what they’re doing.

[00:11:30.500] – Joran


[00:11:30.810] – Joran

And I think in your case, like, you need to have a vision, you need to be ahead of the market. Right. Especially in cybersecurity, you can’t just build what the customers are asking, because otherwise, like, you’re not helping them to fight against the new cybercrimes, which are happening tomorrow and the day after.

[00:11:45.680] – Jamie

100%. Yeah. And I think there’s so many examples. If you look at financial services or fintech, some systems just fundamentally broken and they need to be rebuilt from the ground up. Waiting five days for a payment to go across the world, it’s just bizarre. That needs to be sorted. The whole process of buying a house or renting a house, all these things that are highly inefficient, highly manual. That’s why you need to be really strong in your product vision, because otherwise you’ll never. You just make. You make a faster horse. Right?

[00:12:18.300] – Joran

Exactly. A faster horse. Nice. When we dive into your go to market strategy, like, how did you go to market? How did you approach things?

[00:12:27.220] – Jamie

So it’s adapted quite a lot for us over the last seven years. So we started with direct go to market, and I actually still think that’s a pretty solid way of starting. And over time, we evolved into channel first. So last two or three years, we really started doubling down on channel. So channel being resellers, manage service providers for us.

[00:12:47.210] – Joran


[00:12:47.880] – Joran

And how do you then, because in the beginning you said, like, talk to your customers. How do you still make sure that you talk to the customers if it’s channel first?

[00:12:55.860] – Jamie

It’s a real challenge. I think anyone that’s considering building a channel part of the business, or even going channel first at the start, I’d say find some way of closing that loop with the customer, with the users, whoever is like ultimate beneficiary of the product. The way we do it is we still have about a thousand direct customers we can test, experiment with. We also ask our partners for feedback. We do a lot of feedback sessions directly with end users as well. So we try and basically keep your ear as close to the ground as possible.

[00:13:25.840] – Joran

Exactly. So don’t rely fully, I guess in that case on partners, but always make sure that you still hear it direct from the 100%. And I guess if you look at the go to market, like what has been, for example, one thing you did really well, which has been pivotal for your guys success.

[00:13:42.080] – Jamie

I think one of the accelerants for us, and it’s probably not applicable to everyone, but for us it was distributions to resellers. I think that really opened our eyes up to what was possible with channel, because we had our own channel before then, but we weren’t really running a channel program. We hadn’t really sat down and thought about that. We didn’t have expertise, the company to actually know that route to market well enough. Distribution helped to navigate like product communication, cadence, how to manage channel partners, how to incentivize them really was a bit of a crash course for us in reselling. So that was one I’d say was an accelerant for us.

[00:14:21.300] – Joran

Yeah, because it’s not the most common route. Because you’re self serve, at least product led growth, and then you’re doing it via channel. Maybe any learnings or any key takeaways which you can give to other SaaS founders now listening where this is not the most typical thing to do, right? Or am I wrong here?

[00:14:37.850] – Jamie

I’d say we were talking earlier about this, about building channels, and I think, and if you want to do it quickly, if you don’t have five years to build a channel, and I do think it takes many years, like you need to maximize your exposure to different types of channel partners. And if as a founder, you need to be the one leading that, that’s an understated fact. Something that I didn’t realize at the start is whenever you’re trying to do something, like completely new to the business, like you’re usually the best place person to do it because you take all your knowledge, all your experience, and you can very quickly adapt and iterate. If you go and hire someone who’s ten years experience, 20 years experience doing channel, drop them in, give them your product, it’s basically not, it’s a recipe for disaster. They’ll come back like six months later, they might have made progress and then you have to start the cycle again. So I think, yeah, immerse yourself in it.

[00:15:26.870] – Joran


[00:15:27.140] – Joran

And I think there’s a good, like, overall feedback. Whenever you want to do something new, dive in yourself first, at first as an entrepreneur, and then if it works or if it goes well, then you hand it over as a project, I think.

[00:15:38.860] – Jamie

I’m not sure if that is great advice, but it’s definitely what’s worked for me.

[00:15:42.470] – Joran


[00:15:42.850] – Joran

But I can already learn that your mindset, as in, as you said, you’re unemployable. You want to feel, figure things out and then probably when it’s working, it loses your interest in a way, maybe where you want to fix challenges, fix problems and then dive deeper.

[00:15:57.520] – Jamie

Yeah. You’ve got to stay on the problem long enough for it to become something that’s repeatable, I think. And the benefit then is actually you have experience, you have perspective of that. So when you are hiring people into the role, you can actually tell them, what does it look like day to day? Would success look like, what are the failures? And when they’re coming back to you with new objections, new challenges, or they’re trying to push it in a different direction, you can speak from a point of perspective. So, like, me immersing myself in channel allowed me to actually become more fluent in that conversation. When you’re hiring professionals.

[00:16:31.510] – Joran


[00:16:32.490] – Joran

And when we look at the journey, what has been your biggest company challenge so far?

[00:16:37.970] – Jamie

I think, I don’t know how many people say this on podcasts, but big challenges always revolve around people. I think especially if you’re like venture backed, you’re going to be going through cycles where your company’s going to be evolving and will look materially different year after year. Like definitely every two or three years, it’s going to be a materially different company. You might have changed your go to market, you might have changed your product offering, you might be serving a different end customer. And all those are going to. Not necessarily, but a lot of them will lead to changes in people. And so I think all the challenges, all the major ones, I’d say around rebuilding teams, bringing the right people for the right time, right phase of the company as well.

[00:17:17.650] – Joran

Yeah. Yeah.

[00:17:18.500] – Joran

Because that’s what I experienced at least. Personal, right face of the company. I think, like, you have a lot of people who want to work in an early stage company, but when it gets too big, too many processes, HR becomes bigger, too many more rules come in, that’s where I go. Not so well either. Like this crappy part and is that something like you see it’s more as in that, but also all the other things you mentioned. I guess with the things changing, the team will change as well.

[00:17:45.480] – Jamie

Yeah, 100%. As soon as you start, you change your go to market, especially if it’s as radical as going direct to customer. For example, you might built up a team of bds and sdrs for example. And you don’t need those necessarily in a channel model.

[00:18:00.290] – Joran

Yeah, makes sense.

[00:18:01.440] – Commercial Break

Are you struggling to find a cost effective and scalable marketing channel? Check out Reditus. We help you to have other people recommend your SaaS and you would only pay them when they deliver. You paid clients, making it a very cost effective and scalable marketing channel. Want to learn more? Go to getreditus.com.

[00:18:18.660] – Joran

When we talk about personal challenges, like everybody hits rock bottom at one point. What was your moment? And I guess like how did you get out of that?

[00:18:28.000] – Jamie

I can remember one moment, that was what, six years ago, standing on the rooftop. Don’t worry, I wasn’t going to jump.

[00:18:35.480] – Joran

I was already asking.

[00:18:37.000] – Jamie

I was standing on the rooftop. It’s when my co founder and I decided we were going to part ways because I wanted to go and build a VC backed, high growth, high risk company that may change the world but may also crash and burn. She wanted to build an organic, very successful company as well, with the same aim, same purpose, in a different, slightly different direction. And I think that was that realization that, oh no, this is me. Back then I had a strong core team around me and we brought in some really excellent people after that that helped us get through that and rebuild. But it’s okay, I’ll rest on my shoulders now. That’s quite a big solo founders out there I’ve got a lot of respect for. It’s probably one of the hardest things to do.

[00:19:17.330] – Joran

Yeah, but as you mentioned, at least you got help in, right? So whenever you made that decision, you got the help in to make sure you actually make the right calculated decision.

[00:19:26.680] – Jamie

I think, yeah, you need you support, right. You’re never going to be ten out of ten in everything. Like people go to market, product, operations, finance. Right. You’re going to these core areas of the business. You’re going to need people have expertise. You might be able to cover two or three very well, but you won’t be able to cover all five all the time. Like really look at whether you do a responsibility matrix or you just do a simple, here’s what I’m good at, here’s what I’m bad at. Here’s what I like. Here’s what I hate. Just do an exercise like that I think can help you to figure out, right, what kind of person, what kind of role would really complement this.

[00:20:02.370] – Joran

Yeah, I think it’s a really good exercise. Like, I haven’t done it even personally myself, but I think by understanding yourself a lot, you can also figure out, like, who do you need around you. Yeah.

[00:20:12.450] – Jamie

And ask for feedback. Because we’re like our. The worst judges of our own character, I think. I think if you ask people for the weaknesses, particularly. Right. Because I think strength should probably get a good idea of what’s good. But ask people like your team, your friends, your family, your spouse, your partner will definitely tell you the truth.

[00:20:31.540] – Joran

In my case, she’s going to be really honest. So that’s nice. If we talk about failures, we love learning about failures, mistakes, things like that. What has been your biggest failure? Mistake?

[00:20:42.250] – Jamie

This is a hard question. I think probably this is a little, like, over time, I’d say it’s more of a problem in a single point if you don’t invest in yourself. And when I’ve not invested in myself by that personal development, growth, my own skill set, have I got the skills that I needed to be a CEO of a company that is five people? Yes. Do I have it for 20 people? No, not at that point. So you need to grow and then for 50 people. And I use people as. There’s a good way of thinking about it, because the way the company communicates, the amount of information people know, like everyone in the team as well as like, varies drastically. So I think you do need to change a lot is how you communicate all that kind of stuff. And I think not investing myself always led to, like, pain and friction down the line when stuff has happened. Oh, yeah, you can’t. You got 20 people. You can’t know every single deal that’s going on. You can’t know every single product feature. You can’t review every line of code, which I was doing.

[00:21:37.850] – Jamie

You can’t do these things. You have to let go. It’s probably another big personal learning or failure is like holding onto stuff for too long. I think it’s good advice. I never listened to it. I don’t think many people listening would either. But if you can do let go.

[00:21:54.990] – Joran


[00:21:55.370] – Joran

Because I think it’s really nice to hear, or it’s nice to hear somebody say, let go, but actually do it.

[00:22:00.890] – Jamie

For me, the key’s always been bringing someone that’s. That can do it better than you. That’s the easiest way to let go. Find someone that can do that thing better than you can. Like finance, for example. Got amazing CFO. I just don’t even think about it. The more that you have competent, capable people around you that you trust, the easier it is to let go.

[00:22:19.960] – Joran

Yeah. Yeah.

[00:22:20.670] – Joran

And I think that’s a really good learning and a really good way, because indeed, if you don’t trust a person to do better than yourself, you still want to check everything.

[00:22:29.770] – Jamie

That’s not a good place to be.

[00:22:31.210] – Joran

No, exactly. When we look at company wise again, if you could go back in time, is there anything you could. You want to do differently?

[00:22:40.590] – Jamie

I think we’re quite lucky because we’ve had quite a long time to develop and adapt and learn. I’d say probably the thing I’d love to do more of and the stage that I enjoyed, that small, nimble stage, like under 20 people, even under ten, where you’re just. You’re constantly learning and adapting. I think stay there as long as you can is probably my advice, because I think there’s so much value and adaptability, learning and your burden rates modest. You can go a long time. There’s often a kind of. There’s a lot of, like, almost like peer pressure, right. As a founder, to be like, oh, we should raise money. We’ve got to ten or 20k, we’ve proven our initial, we should raise some seed or some angel or, money’s really tight, or, this is really stretching the resources, or we can’t keep up with customer demand or something like that. And there’s always a strong pull to grow, grow revenue, grow headcount. And I think resisting that to really solve the problem, it benefits, it pays off in. It’s an investment, really, in the future of the company.

[00:23:44.850] – Joran


[00:23:45.610] – Joran

And indeed, as you mentioned, it’s a lot of peer pressure because any event.

[00:23:49.520] – Jamie

You go, oh, my gosh, how much money you raised? Like, when. What’s your ar. When are you going to do this? What’s your next milestone? There was actually a really interesting talk at SaaS. Open talking about like this, is anyone here flat or not growing? And quite a lot of people said, yeah, a lot of people really want to get out. It’s like a really uncomfortable state to be seeing a revenue year over year being the same. But I think you need to find, like, where are we learning? Where are we growing? What capabilities, what skills are we developing? What have we invested in that is going to pay off ten x in the future? I think look at it a different way. We simplify stuff too much. I think headcount and revenue.

[00:24:29.100] – Joran

I do it even in the podcast. I don’t know if I personally like it that much, but it is nice to get a grasp of where’s the company? What kind of problems are they having right now? But I do agree to any event you go, I even had one person at the drinks that starts open. Ask me. It was their first question. They asked me even introduce yourself, what is your ar? Is that really your first question you’re going to ask me?

[00:24:51.700] – Joran

That’s funny.

[00:24:52.410] – Joran

When we look about Cybersmart, have you been using any kind of processes, strategies to get to the point where you are today?

[00:24:59.630] – Jamie

We’re obsessed, I’d say is probably a good way of putting it. When it comes to operations, we’ve got an awesome director of operations as well. Before that we had an epic CEO that came in and helped us rebuild all of our information hierarchy, all our ways of working. And we did that really early on, like when we were smaller. And then it grew with the company, which was nice. Like we started with okRs. We’re probably what, five years into OKRs running those. We actually moved to a four month OKR this year. It’s quite interesting. I’ll let you know how that goes. From quarterly we’ve implemented four DX that’s been really good for things that are not like mission critical. We’ve got to do something really uncomfortable. OKRs are great for moving into new territories or new markets or new products. Four DX has been really good for more of the business as usual. So we used to call it Bau and PMF business usual product market fit, pretty weird, but essentially everything that was like more drumbeat. Like once you’ve got a go to market, motion repeating and building that, measuring it weekly basis, etcetera.

[00:26:05.520] – Jamie

Even pulled some stuff out of the entrepreneurial operating system or the EOS might have heard attraction. It’s a great book, pulling out these meetings from their meeting cadences. So we spend a lot of time and effort really optimizing for systems, processes, communication. And I think the reason we spend so much time is cadence matters a lot in a startup. The drumbeat that you’re creating is how people show up to work. It’s what people aim towards. It’s like when deadlines get set, whether stuff gets done or reviewed, etcetera. I think the really big one where you’re doing stuff like ok, if you’re doing it properly after a few cycles, no one ever gets the right start, is that you really get towards clarity and what you’re trying to achieve because you’ve been like, we want to launch a new region. Okay, what does that mean exactly? How many customers is that? What type of customers is that? What products are they buying? Are we talking our current product in the new market? What’s the ICP look like? So it forces you to get really clear. So cadence, clarity, and then the last one it is, it gives you confidence in being able to achieve those outcomes.

[00:27:13.960] – Jamie

Like pre okrs, we just say we want to get to 1 million ARR by the end of year one. We just started, so obviously we’re never going to get there. We had no idea about how we’re going to get there, how many customers that would be like, what was needed to get there, who was needed to get there. So we was just like a hope, really. And I feel like a lot of goal setting can be. Just be hopeful. And I’m not saying don’t have your big, hairy, audacious goal or whatever, still aspire to your moonshots, but when it comes to executing, I think you need to be super clear on what you’re trying to achieve. So I’d say those three areas are really important when it comes to goal setting.

[00:27:50.930] – Joran

And you took it from different systems. You mentioned EOS, okRs, then the 40 x, so you combined it to what’s working for you 100%.

[00:27:59.470] – Jamie

I think that’s the most important thing. And never take a framework and just drop it in. It might be helpful if it’s your first one, like EOS, and just drop it in and try and run it as it’s intended. But we’ve always adapted and said, what bits of this work well, what don’t work so well? And iterate. We set up a new meeting and as what I said was like, the only thing I know is this is not going to be the right format, but we are going to iterate on it. So you have to have that mindset of learning if you’re never going to get it right in one quarter or one cycle.

[00:28:28.730] – Joran

Yeah, yeah.

[00:28:29.550] – Joran

Makes sense, makes sense. And have there been like, in your journey, any pivotal moments or I guess like critical decisions you made which got you to the point you are right.

[00:28:41.240] – Jamie

Now, I gave a talk on this two weeks ago in SS open.

[00:28:46.150] – Joran


[00:28:46.330] – Jamie

The free bold moves. I probably say that the biggest pivotal moments have always to do with people changing the gods. We talked a bit about that as well. And then the go to market change, this big one, I say the other one really is like the choice of how you fund and grow the business. So whether that’s bootstrapped or venture backed or something in between, I think that was a big one for us. We decided that early on and stuck to that.

[00:29:14.150] – Joran


[00:29:14.620] – Joran

It’s kind of almost like summarizing it as making hard decisions, because letting go of people is not easy. Changing your go to market is probably not easy as well. You have to make a hard decision to 100%.

[00:29:26.460] – Jamie

Yeah, I think a lot. Like almost the data is easy.

[00:29:30.800] – Joran


[00:29:31.120] – Jamie

We should obviously serve more of those types of customers, or obviously we need to adapt and grow. All the data is often easy bit, and the hard bit is the execution piece. Like bringing everyone with you on the journey. Like, we were talking to one of the founders earlier about them merging companies. And so the decision to merge the companies. Yeah, it makes sense. Synergies, etcetera. We can combine efforts, combine product resources, like 80, 90% of m and a fails. Right. Because you’ve got the whole year long cultural integration, and nothing’s really as rosy as it looks on the surface.

[00:30:06.220] – Joran

Yeah, yeah.

[00:30:06.970] – Joran

And I think that’s where you mentioned again with the okrs, you have clarity, so at least people know where they’re going towards and you have your vision, your goal, so at least you can guide them, guide everybody into a certain direction.

[00:30:18.820] – Jamie


[00:30:20.030] – Joran

We talk about process, we talk about company processes, but how do you manage yourself, or how do you manage your time?

[00:30:26.260] – Jamie

I’m really strict about time blocking. So, like, my calendar is basically how I run my life, personal and professional. I literally just show up at the time. That stuff’s in my calendar. So in order to achieve that, you need an epic assistant or a chief of staff. I have an epic assistant who basically makes me incredibly organized. I’d say triples my productivity least. And just by helping me to make sure I’m in the right place at the right time, doing stuff that matters. Right. That’s also one aspect, is you can often go into this whirlwind of lesson four, DX, or the whirlwind of day to day activities. Spend all your time doing emails or something like that. And so I think getting an EA or someone that can really support you in that is super important. It’ll give you superpowers as well. I think that the big challenge as a founder is, like, letting go of the stuff. We talked a bit about that, but actually thinking and spending the time, what is the thing that only I can do? I think that’s part of my journey I’m going through now. Is we’ve got leaders, so I’m leading the leaders, and I’m also spending time thinking, what can I uniquely do?

[00:31:31.410] – Jamie

Really? What can only I do? And that’s the stuff I’ll try and do more of.

[00:31:35.570] – Joran


[00:31:36.030] – Joran

And that’s, for example, also, I guess you have in your calendar figure out or not, it’s not going to call like this. How can you take the company forward? So really deep learning, maybe and 100%.

[00:31:46.860] – Jamie

Yeah. Like, literally, I put a whole day called deep zone. Okay, lock it out.

[00:31:51.090] – Joran


[00:31:51.650] – Joran

And then from there, you can, like, how do you, I’m curious now, how do you start, like, you just deep zone. And then from there you have notes where you want to dive into certain things or.

[00:32:01.170] – Jamie

So this is, I don’t know how common this is, but for me, I always get ideas or thoughts when I’m, like, doing random stuff that, like walking somewhere. I’ll go into the gym or something, I’ll be, like, sitting. It’s like running on the treadmill, and I’ll stop the treadmill right down something because I just come up with an idea. But then when I get to that time block, I’ve got, like, a bank of stuff to work through. I think it’s so easy to be like, open slack, respond to messages, check your email, and then all of a sudden your day’s gone and you’re like, I didn’t actually achieve what I wanted to have that bank. I think the other thing, the other concept, I think has been really helpful for me is that a flow. So once you’re in flow. So I think it’s tits. And Mikhaili invented this concept around, like, people getting into the zone, basically in an area. I think if you’re feeling creative, do creative stuff. If you’re not feeling creative or you’re not in the mood to think about the strategy of the company for the next three years, then don’t do it.

[00:32:58.180] – Jamie

I think, try and find that time when you are you feeling the pull, right? And that’s when you’re gonna come up with the best ideas. So although you’ve got to be really strict about your time blocking, I think also you’ve got to be mindful of, like, when you’re in the mood to do stuff.

[00:33:11.000] – Joran

Yeah, indeed.

[00:33:11.630] – Joran

Because it doesn’t have to be a must. You want to do it and you want to have the ideas. But I like the bank idea where you have a lot of ideas. I guess you get sometimes during the days, right, like after a call or during a call. And then you probably want to take it like right away to somebody or you want to do something with it, but by writing it down and actually taking it in the desiccated time, then you can think about it more. And maybe you think it’s not actually a priority anymore because I have all these other things I want to investigate first.

[00:33:38.290] – Jamie

Yeah, it’s a really good kind of related to that is just having the time and space to think through stuff is really important. So even though you blocked out your calendar, make sure you’ve got some free space in there as well. I often, if it’s during the work day, I’ll just like ping my CFO or using my CFO because it’s been my sounding board for the last six months, essentially. Oh, I’m thinking about this. Or it’s often like a crazy idea and doesn’t work, but just the process of getting it out, you refine it, you get a bit of feedback on it, and then you say, oh, I’ll take that away. And then a week later I’m like, okay, I thought about a bit more. This is what I’m thinking now.

[00:34:17.120] – Joran


[00:34:17.560] – Joran

And I guess I like it. As you mentioned, that you’re sparring with somebody all the time. Also, even though you mentioned now solo or being a founder, you don’t have to do everything by yourself. Find those sparring partners who know things better than you, like your CFO you mentioned on the financial part. Make sure you use them.

[00:34:36.000] – Jamie

Yeah, I think it’s too easy to fall into that trap of being like absorbing and taking everything in and becomes a bit of. Bit of a labyrinth sometimes because you’ve got like all this information and knowledge and ideas and it can fill a bit circle. I think getting out, speaking to people, other founders, I think is a really useful source because people have perspective on your ideas and I think just speaking about them, it’s like a, it’s like a ball of clay or something. You need to mold it until it looks good, right?

[00:35:04.310] – Joran

Yeah, yeah.

[00:35:05.190] – Joran

If only you can go to the moroccan desert with 40 founders, just ride a camel and talk about SAS.

[00:35:10.340] – Jamie

Yeah. Now this is important. This is refreshing. Recharging, come up with the next good idea or improving your existing ideas. I think last couple of years, a lot of it’s been about really figuring out what works and really fine tuning as well. So it’s good sessions for that.

[00:35:26.610] – Joran

Yeah, love it.

[00:35:27.830] – Joran

We’re going to dive to the end the three final questions. So if you can give a SaaS founder advice, who is just starting out on their journey, going from one to ten k monthly recurring revenue. What kind of advice would you give somebody here?

[00:35:41.120] – Jamie

I give some generic advice and then our advice or our story as well. So for me, generic stuff, I’d say that phase is all about failure or unplanned learning, however you want to look at it. But it’s trying lots and lots of different stuff. And that can be with the product, it can be with the go to market, it can be with a team. It’s like a really creative space. I’d say it’s where you figure out what works, what doesn’t work, and I think you have to be super willing to adapt and pivot what you thought was true. So you’re almost at that point, your brain is like 100% open and receptive. And I think as you grow past that, you obviously need to become a little more narrow in your focus. So trying lots of stuff, iterating a lot because you’ll never get it right first time. And I think often we’ll fail if we try something 510 times. Like, we called 200 partners once we realized the potential in channel, we called 200 partners to book 40 demos. So, like, we, a lot of people would have made five or 1020 calls and been like, this isn’t right for us.

[00:36:47.070] – Jamie

But by iterating, then we’re able to get the script better, figure out what a good partner could look like, etcetera. So the last bit, I’d say, in that stage is just perseverance, because, like, it’s nice to have that ten K goal in mind. I think it’s almost better, like, coming back to what we’re seeing earlier about these numbers. It’s almost better saying, what do I need to learn or prove to move to the next stage? And ten K is probably a nice, simple way of doing it. Actually, it’s a bit more like, I want to have ten customers that tell me this product is, they couldn’t live without this product. Right. Like the Shaun Ellis product market fit test, something like that. I think that’s a better milestone almost than a revenue.

[00:37:24.300] – Joran

Yeah, no, I agreed, because you need to have happy clients who can’t live without your product anymore, who can help you to the next phase.

[00:37:31.450] – Jamie

Exactly. Yeah. Money will always fall, I think, if you can create customer value.

[00:37:35.450] – Joran


[00:37:36.110] – Joran

Did we go beyond the ten k monthly return value? And this is a huge step, I know, but we’re going to go to 10 million ARR. What kind of advice would you give SaaS founders here?

[00:37:45.160] – Jamie

I’d say probably like the two big things actually three things. So the first one would be information hierarchy. It’s not a technical term. Basically, how do you get information from the team and how they take decisions? How do you cascade information down top to bottom, but also how the teams work between each other. Product and engineering. Easy. One product engineering or technology team and your good to market team. How do those two areas work together? I think spend a lot of time iterating and improving how information flows. So it’s not just about like presentations or one way communication, it’s all about like tools and mechanisms to create that. I think the, the second big bit, and it’s quite. It’s related kind of what I’m talking about there. It’s the culture, I think, over invest in culture because it’s something that is so important for attracting people, it’s so important for retaining people, it’s so important for change management. And change management is happening throughout that whole cycle. You’re still going to have ten k to 10 million. There’s a lot of change management. So investing in culture, in other words, like, why are we here?

[00:38:54.700] – Jamie

What do we want to achieve? What does good look like for us? What the shared set of values and beliefs we have as a company and not putting that as a second priority. So that’s always been really important for me from day one as well. And the third one is more of a personal one, I think. And it actually ties up nicely to what we were saying before. As a founder, you need to constantly look at what you’re doing and do less. I think it’s something I’ve constantly struggled with as well. But, like, focusing on yourself, like, you’re not going to get one to two to three to five to ten if you’re always in the weeds, like, you won’t be able to see it.

[00:39:28.530] – Joran

Yeah, yeah.

[00:39:29.130] – Joran

And with do less, you mean be less in the day to day, but focus more on the things you mentioned, like the division, how do you get to the next milestone?

[00:39:37.790] – Joran


[00:39:38.030] – Jamie

And I was lucky because I had people around me telling me to get out of our day to day. You shouldn’t be rankoed, you shouldn’t be selling, you shouldn’t be doing this. Don’t do your job. Think about what’s coming next. What are we doing next quarter? That’s what we need to know. What’s the plan for the year? What happens if we don’t get, what’s the next move we’re going to be making? So, like, the team need that from you far more than they need you to come in and make a difference, you will have marginal gains. In fact, you’ll probably slow people down at that stage.

[00:40:06.010] – Joran


[00:40:06.530] – Joran

And to come back to what you said before, if you have the right people who are more knowledgeable on the thing you want them to do, then there’s no reason for you to go in anymore. Yeah, we dive into the last question. Any final thoughts, learnings you want to give away to other SaaS founders?

[00:40:22.080] – Jamie

So I was on a panel last week and someone was talking about their challenges, and the advice I give them is stick with it. I think it is really hard starting a company. Look at the failure rates and the successes, etcetera. You’re in the minority if you can get through all of that challenge. And I think it’s often easy to let the failures and the things that don’t get right overwhelm you. The most successful people have been through hundreds of knockdowns and setbacks. I think stick with it is probably my number one tip.

[00:40:57.420] – Joran


[00:40:57.830] – Joran

And stay quivered. It’s an english term, right?

[00:40:59.750] – Jamie

So it means stay with perseverance, adaptability, like pushing yourself into uncomfortable places, taking difficult decisions in order to progress forward. So, yeah, have grip. It’s probably the american way of saying, nice.

[00:41:15.460] – Joran

Nice. Cool.

[00:41:16.770] – Joran

This was the end. What we’ll do is we’ll link towards Cybersmart. We will link towards your LinkedIn profile, because is that going to be the best way to contact you if people want to reach out?

[00:41:26.480] – Joran


[00:41:26.920] – Joran

And we’re going to link to watch the three processors you mentioned, Eos, okrs. Okrs and then four DX. Thank you. And if you’re listening on Spotify, make sure to hit follow and leave us a review there so we can help other SaaS founders on their journey. And I think we’re now almost going into the desert here. Thank you for coming on, Jamie.

[00:41:45.590] – Jamie

Thank you.

Joran Hofman
Meet the author
Joran Hofman
Back in 2020 I was an affiliate for 80+ SaaS tools and I was generating an average of 30k in organic visits each month with my site. Due to the issues I experienced with the current affiliate management software tools, it never resulted in the passive income I was hoping for. Many clunky affiliate management tools lost me probably more than $20,000+ in affiliate revenue. So I decided to build my own software with a high focus on the affiliates, as in the end, they generate more money for SaaS companies.
Share the article:
Scroll to Top