When to move from founder-led sales?

In the beginning

In the early phase, founder-led sales are often the best route. The founders have the passion, knowledge, and authenticity to excel at sales. They can explain the value proposition, answer objections, and even commit to product improvements in the moment. The bottom line is that their belief in the mission is attractive to the buyer.

However, there comes a point when hiring a professional makes more commercial sense. Getting the timing right is not easy. Switch too late, and you miss out on commercial opportunities; switch too soon, and there’s a high chance the hire won’t work out.

What are the Signs? There Should be push and pull in play

Push signals are that the founder’s role is increasingly strained. More sales and wider founder responsibilities make it all too much to pack in. Imagine a diary with constant clashes between sales activity (prospecting, discovery calls, demos, proposal writing, key client calls) and dev and product team demands. And that’s before the strategy, funding, hiring, and leadership tasks… (and a bit of me time!)

Not only should it feel time-constrained, but there will also likely be a nagging feeling of high-value vs low-value tasks. While sales matter, not every activity under the ‘sales’ title is high value. Could effort have more impact elsewhere?

Another aspect is the founders’ network. How much of it has been plundered to date? Does the founders’ network constrict sales volumes and velocity? If so, that is another sign that it is time to bring in a more dedicated resource.

Key Performance Indicators

 Before making the transition, establish clear metrics that indicate readiness. Your pipeline should show consistent growth with predictable conversion rates across stages. Track metrics like sales cycle length, win rates, and average deal size. These numbers provide crucial benchmarks for future sales hires and validate your sales process.

Cost considerations and structure

Understanding the full financial impact is crucial. Beyond base salary, consider commission structures, sales tools, travel expenses, and training costs. Build a compensation package that aligns with market expectations while ensuring it scales with your business model. Your budget should accommodate at least 12 months of fully loaded costs.

Onboarding Framework

A structured onboarding plan increases the likelihood of success. The first 90 days should include deep product training, shadowing founder-led sales calls, introductions to key customers, and gradual handover of pipeline opportunities. Set clear milestones for independence and revenue expectations that align with your sales cycle length.

Setting up for success

There should be enough to attract a new sales leader and set them up for success. Typically, this is a one-person gig. Finding a full-cycle salesperson is not easy; just dropping them in and expecting success is doomed to failure.

The basics need to be there: brand foundations, market segmentation, agreed value proposition, and early adopter customers to shout about.

But that is not enough. Have the key people been identified in top target accounts? Is there a volume of data being amassed? This direction is needed to speed up sales professional outreach.

The salesperson cannot operate effectively without support. They will need a ‘minimum viable’ set of sales collateral – pitch deck, website, capability statement(s), features and benefits, client quotes and proof, and ideally a few longer-form case studies.

Competitive landscape

Your market position affects hiring timing. Do some digging on how competitors structure their sales teams and what experience levels they target. This insight helps determine your hire’s seniority and compensation requirements while ensuring they can effectively position against established players.

Brand matters

All of this will accelerate faster if brand recognition exists in the target market. Has the brand built a position of authority, niche expertise, and/or disruption in the market? If not, the salesperson is just another voice in the wilderness.

That in-market recognition rarely happens by accident. A successful salesperson will work well with marketing, pulling in the same direction. For that to happen, there must be a marketing strategy and a budget to deploy the corresponding tactics.

Summary

To give the sales hire the optimal chance of success, the timing needs to be appraised AND the foundations need to be in place.

Consider the following when looking at the transition from founder-led sales:

• Founder diary under siege with competing demands
• Sense of low-value tasks interrupting higher-value opportunity
• Clear target market segmentation and target data being amassed
• A level of brand recognition in those target market(s)
• Set of sales collateral in place
• Customer-proof stories and case studies secured
• The budget for the hire secured
• Marketing strategy created and budget allocated to deliver it

If the answers are yes, it’s time to draft a JD. While the real world means there’s never a perfect lineup, it might not be the moment to make the switch if most of those are not being met.

Of course, moving away from founder-led sales and bringing in the salesperson does not mean the founder can abdicate the sales process as a whole. The founder is still part of the process, can be present on crucial calls, and can support decisions on pricing, roadmap, and deal elements in the background. These are high-value tasks that deserve their place in the diary. The ‘everyone is in sales’ mantra lives on.