Hi friends - I am officially coming back from maternity leave in 2 weeks and it feels…pretty good!

Baby Luca has already grown SO much in 10 weeks and is melting my heart with his new smiles and natural mohawk. 🤘 

Rich’s article this week is one near and dear to my heart! Founder led sales transitions are so delicate and honestly…really hard. But there are plenty of people and strategies to help ease the burden a bit.

Enjoy!

The Founder’s Transition Playbook: From Heroic Selling to a Scalable Revenue Engine

In the early days, founder-led selling works.

You are the pitch. You know the product better than anyone. You can win trust in a single conversation, and you will run through walls to close a deal.

As one founder put it to me recently, “I’m the SDR, the AE, the CRO, and the CEO all rolled into one, and if I’m not selling, no one is.”

That is fine, until it is not.

What got you here will not get you to repeatable, scalable revenue. The same heroic effort that fuels your first wins can become the bottleneck that stalls your growth.

The Heroic Selling Phase and Why It Breaks

Heroic selling is founder magic, a mix of hustle, relationships, and deep product passion. It is often why you survive your first year.

But there is a limit.

Mark C Ward, Founder of Revenue Arc, described what happens when that limit is hit:

“Between £3 million and £30 million ARR, I’ve never seen a business not have to rebuild its revenue operating model… forecasting becomes ‘hope strategy,’ relationships between sales, CS and product start to fracture.”

I have seen it, too.

A founder hires their first sales leader, but nothing is documented. All the nuance, what works in the pitch, which objections kill deals, how to navigate the ICP… is in the founder’s head.

Within months, the pipeline is flat and the founder is back in every deal.

When to Make the Shift

Dan Hurwitz, Fractional CRO (now AI Infrastructure Sales Leader at DDN), summed up the three signs it is time to move from founder heroics to a scalable GTM:

“You’ve got a handful of paying customers, you’re starting to see repeatability, and you’ve got a clear enough ICP that someone else could run with it.”

Another (more painful) sign? 

You are burning out.

If every deal still depends on you, you are not just blocking growth, you are risking the company’s ability to scale at all.

And as Jess put it in our recent Making Revenue Tick podcast,

“If you’re still the one chasing every deal at this stage, you don’t have a sales leader, you just have support. You can’t scale if all the revenue still depends on you.”

The Scaling Toolkit

Here is what I have seen work when founders make the leap:

1. Document What Works: Take what is in your head and turn it into a repeatable process. Messaging, ICP triggers, proof points, objection handling = all of it.

2. Map to the Buying Journey: Mark C Ward’s advice: align your sales process to how your customers actually buy. Otherwise you are building the wrong machine.

3. Build the Early Playbook: This does not have to be fancy. It just has to be enough that a new hire could pick it up and run.

4. Hire Multipliers First: Bring in leaders with the C.O.R.E. traits, Collaboration, Ownership, Resourcefulness, Execution, who can sell and build at the same time.

5. Operationalise Everything: Heath Barnett, VP Revenue at Mixmax, said it well, “It’s not about a better CRM, it’s about making the CRM the source of truth so you can see the health of the business without being in every meeting.”

What It Looks Like When You Get It Right

When founders make this transition well, the results are transformative.

Your pipeline is not just full, it is predictable. Deals are being won without you in every conversation. Your sales leader knows how to coach reps using real, data-backed insights instead of gut feel.

You start seeing team members take full ownership of outcomes, finding creative ways to break into accounts, bringing customer feedback into product decisions, and building cross-functional trust.

Most importantly, you get your time back to focus on where you add the most value, whether that is fundraising, deepening key customer relationships, or setting the long-term vision.

One founder I worked with to hire a Sales Lead went from being in 90% of sales calls to less than 10% in under 4 months, without a single dip in revenue.

In fact, in the first 12 months ARR grew by 300% because the new sales leader lived and breathed sales, so after a ramp she became more effective.  And the founder (a product specialist by trade) could focus on building the capabilities which made the tech even better for their ICPs needs.

Traps to Avoid

• The Unicorn Hire Myth: You hire a unicorn VP Sales thinking they’ll do it all, but they come from a place with 20 SDRs and a brand everyone knows… now they’ve got no leads and no playbook.

• Tech Tool Overload: Ten tools will not fix a broken process. Start with discipline, then add tech. If you wait too long to bring someone in, you’re not just behind, you’ve also burned your own energy and you’re starting from zero again.

• No Feedback Loops: Your GTM only scales when product, sales, and CS are in constant conversation.

• The Mindset Shift: Stepping back is not about doing less. It is about making space for the team to operate at their best. You’re not stepping back to be less involved, you’re stepping back to create space for the team to operate… and that’s what scales. You stop being the single point of failure, and start being the leader who builds the machine that wins without you in every deal.

I’ve shared a few podcast quotes in these articles, so let me intro it properly… 

I've created and also host a podcast called What Makes You Tick? Tech Leaders Career Stories. We've run it for 2 years and have released 97 episodes (at the time of writing this).  All focused on GTM leaders and founders sharing their hard learned lessons, as well as delivering masterclasses answering the big questions and challenges around growth in tech.  You can find our channel here:

If you want to go deeper, listen to my conversation with Mark C Ward where we talked through exactly how founders make this shift from speed, to proven operating systems, fit for your stage and context.

See ya next week for the last article in this mini series!

Want to learn more about how I help startups increase their revenue by 150-590%? 👀 

Know someone who could benefit from being added to this distribution? Send them here to sign up!

With love and gratitude,