In the early stages of any company, the founder is a generalist by necessity. You are the product manager, the marketer, the delivery lead, and—most importantly—the closer. There are two reasons for this: First, there is rarely enough money to hire for every role from the get-go. Second, many founders like to get their hands dirty, learning the inner workings of their own machine before they can delegate it.

But if you want to grow, you eventually have to step away from the day-to-day to focus on the vision, direction, and leadership. While this is true for all companies, it is especially true for professional services in AI Enablement.

In the SaaS world, this transition is a celebrated rite of passage. Around the $1M–$2M ARR mark, the "Founder-Led Sales" era evolves into a playbook a team can drive. It is a magical transition where the startup is deemed to have found "product-market fit" and a documented, repeatable sales motion. Suddenly, revenue becomes predictable, signaling to investors that the company is ready to scale.

Many founders describe professionalising the sales motion as one of the greatest challenges in company building. When it comes to SaaS businesses, the transition away from founder-led to a team and playbook-driven sales process has been studied and is well understood. 

But what if you are running an AI services business? Should you still be following conventional playbooks for professionalising your sales team? It is still important to document your process and hire “doers” before VPs. But other generally accepted truths can do more harm than good for an AI enablement consultancy. Below, we examine the similarities and differences between these two types of businesses when it comes to evolving your sales motion away from founder-led sales.

It should, of course, be prefaced that not all AI enablement businesses are created equal. In our definition, AI enablement services encompass three broad areas: consulting, training and implementation. The degree to which you can “borrow” from the SaaS playbook depends on how standardised your product delivery is. For example, if you are selling training engagements, your sales motion (and the people you hire to execute it) will be more similar to a typical SaaS sales motion than if you’re selling fully bespoke consulting engagements. 

In SaaS, the goal is to replace the founder with process and reps. In AI Enablement services, founders stay involved much longer because the founder’s credibility is part of the product. You aren't just selling a tool; you are performing four roles:

The role is much broader in scope than simply diagnosing a problem and offering a standard solution, and requires a different set of skills, which is why even large, successful consultancies run their sales motions differently from large, successful software businesses. 

When you think about scaling your AI enablement business, instead of a total sales handoff, aim for granular delegation, for example:

SaaS thrives on a narrow Ideal Customer Profile (ICP), repeated objections, and standardized demos. AI Services is the opposite. Each deal is a variation where sales blends into solution design. In this world, "discovery" is often consulting work in disguise. You can’t fully hand off sales until you’ve standardized delivery. That rarely happens before $3-4m in revenue. Many firms try to scale sales before they’ve defined what exactly is being sold.

Standard SaaS advice says to hire two quota-carrying AEs before hiring a sales leader. They will succeed if they have the energy and willingness to master the product. But in services, pure salespeople often underperform. The best early hires are "hybrid seller-doers", ex-consultants or principal-level operators who can think on their feet, command respect from functional leaders, and understand the intricacies of project delivery. Hiring a SaaS AE into a services firm often leads to "overselling," which breaks delivery and causes churn via reputation damage.

In SaaS, a closed deal means revenue accrues automatically. In services, sales create a delivery obligation. Revenue depends on staffing availability, delivery quality, and scope discipline. Founders often stay involved in sales not because they love it, but because they are implicitly protecting the firm's margins and feasibility in a way that a quota-carrying salesperson is not incentivized to do.

In SaaS, the playbooks are clear and explicit. You document discovery, record demos, and turn what works into a repeatable process. AI enablement looks very different. The knowledge you need to close a sale rarely lives in a pitch deck or in the ‘buyer context’ field of your CRM. It’s tacit. It’s judgment and pattern recognition built up over dozens of conversations. It’s knowing when what questions to ask. And when to say no to a shiny but fundamentally bad use case. It’s understanding how decisions really get made inside a client organisation, and how to navigate the politics that sit beneath the org chart. 

Because so much of this can’t be written down without losing its essence, shadowing and co-selling end up mattering far more than documentation ever will.

In SaaS, the transition away from founder-led sales tends to follow a familiar arc: the founder hires a VP of Sales, a sales organisation takes shape, and revenue gradually detaches from any single individual. Services businesses evolve along a very different path. Instead of a clean handoff to a sales function, the founder is joined by named partners or principals, and over time the firm itself builds its reputation as a trusted entity beyond the founder.

The true exit from founder-led sales doesn’t happen just because someone new is carrying a quota. It happens when buyers trust the firm, not just the founder they first met. When senior team members carry their own reputational weight and can open doors on their own. And when case studies and delivery track record do more of the closing than personal charisma ever could. That shift is slow and cumulative. In most service businesses, it takes years, not quarters.

Jason Lemkin from SaaStr offers a clean, reassuring heuristic: once two or three reps are reliably hitting quota, the founder can step back. That logic works well in software, where the product carries much of the load and the sales motion is designed to be replicated. Services businesses operate under a very different rule of thumb. You can only truly step back when deals are closing without clients asking for you by name. For many services firms, that moment never fully arrives—and that’s not a failure. It’s simply the nature of the model.

The deeper reality is that in services, the founder is part of the product. The most effective firms don’t try to eliminate founder-led sales altogether. Instead, they push it upmarket, narrow it to the highest-leverage opportunities, and use it deliberately to shape positioning, pricing, and packaging. As a founder building an AI Enablement services firm, you need to scale trust, judgment, and people, not just process. And that fundamentally changes both when a founder can step back from sales and how that transition should happen in the first place.

— Daria