360 views on tech #48: From founder-led selling to hiring a VP Sales

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6 min readDec 13, 2022

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Sequencing Steps from Founder Selling to a VP Sales

by Seth DeHart — Point Nine

Transitioning from founder-led sales to scaling a sales team is a challenging phase for founders. The process itself is unpredictable and often advice is given by people who do not have experience. It isn’t practical to “Just hire a VP Sales, Account Executives and SDRs”. Strategic hires will put stress on your business if not planned accordingly.

In this article, you’ll find a practical approach instead, aiming to sequence things logically and using hypothesis testing in order to increase success rates.

1.Remember it’s an experiment

Early sales teams often have limited evidence that the product they are selling has strong product-market fit. This is why founders are positioned best to believe in their team’s abilities and run early tests based on how things perform. Although data often lacks at this stage, even a few number of clients is a strong starting point. Analyzing customer profiles, acquisition channels and ways to scale should be used to form and test hypotheses. By testing these hypotheses through the sales funnel, teams can learn rapidly and iterate towards a repeatable and then predictable process.

2. Who is your ideal customer profile (ICP) ?

ICP isn’t about the total addressable market (TAM) but rather the group of companies who will love your product right now. Starting very narrow is actually the key to success, as you will start with a loyal client base while using your time and resources wisely.

The ICP is your starting point for testing early hypotheses regarding your future sales funnel. Who are your happy customers? What qualities do they share? How do you qualify prospects in or out of this range? This can be done by building a list of accounts and personas.

3. Run sales experiments with your ICP

Once you have defined your ICP, you can start to set up the foundation of your sales engine. Analyze the ways you obtained your first ICP customers — which value did you put forward to lure them into the sales funnel ? Classify those and test them when prospecting into your ICP with outbound approaches (Linkedin, cold emailing…). If a certain value proposition consistently gets engagements and scheduled meetings, that is a signal of how to add leads to the sales funnel. Replicating what’s working is key as ICPs are supposed to be a highly homogeneous group.

4. Hire a Sales Pioneer

What if you don’t have enough employees to conduct this hypothesis testing ? In this case, you should hire a Sales Pioneer — and this isn’t about titles, like VP Sales or Account Executives. A Sales Pioneer is a top-performing account executive who has ambition, grit and an entrepreneurial spirit on top of sales skills. Most of the time, candidates self-select into this role because they are willing to cover everything: building lead lists, prospecting, managing and closing deals. An ideal profile would be around a year of experience as a SDR and then two to four years as an AE in startups. This is because this role should combine the building-executing skills of a SDR and the closing skills of an AE.

5. From Outbound Signal to Outbound conviction

As you test your hypothesis on the best ways to generate leads, you also need to look for success signals. More signals means more conviction regarding your sales strategy, which will encourage you to add resources to efficient experiments.

The key to the Sales Pioneer’s success is to begin by building an SDR playbook. This is because SDRs often don’t have enough experience to find and exploit signals the way an experienced AE can. On the other hand, many AEs don’t want to do SDRs’ work or set up a process for them. Someone has to lead the way first.

How can the Sales Pioneer build this playbook ? The first step will be all about iterative learning, by shadowing the founder or the person who’s been selling to the first few clients in meetings. As the Sales Pioneer shadows more meetings, they will find out best practices and signals, leading to a matured playbook. This is when the Sales Pioneer can start taking less qualified meetings to practice selling solo. Ultimately, they will take on more qualified leads with the founder in shadow. If the opportunities generated from the Sales Pioneer are progressing through the funnel, then the team has te conviction to hire one or two SDRs — who will be trained by the Pioneer themselves.

6. The Math of a Sales Funnel: Repeatable becomes Predictable

As the sales team grows and collects data, the conversion rate from prospects to booked discovery calls is a good indicator of whether the SDR playbook is effective. If you can repeat a process and book meetings and then other team members can replicate it, what was repeatable becomes predictable.

It’s also necessary to track how many discovery calls progress to the next phase of the sales funnel, and most importantly how many deals are closed. This is what builds true conviction.

If the SDRs can book meetings for the Sales Pioneer and he or she can close those deals using what they’ve learned from the founder/seller, that also becomes predictable. Layering in the average sales cycle length and average contract value gives very valuable information on the economics of the sales funnel.

Combining all these funnel metrics starts will clarify the ratio of SDRs needed vs AEs for the AEs to achieve their quotas. Such early insights will help inform how future goals are set for both SDRs and AEs — and eventually the Head/VP of Sales.

Once you have these conversion numbers with a large enough sample size, you will have the keys to both raise more capital and more importantly the keys to scale.

7. VP Sales and scaling: the final step

Early on we didn’t recommend hiring a VP Sales as a first sales hire because it can be very expensive without proven results. However, if the previous steps are put into place, you have at least a proven playbook. You now have three options for a strong VP Sales:

a. Promoting the Sales Pioneer into the VP Sales. Pros: they have experience building and leading the company’s sales strategy. Cons: they may not have enough leadership experience when scaling rapidly.

b. Hiring a VP Sales. A VP Sales is reliable because they have demonstrated previously that they can scale a sales org. Their selection should be done carefully and with reference calls on their previous organisations.

c. Hiring a Head of Sales. A Head of Sales is a junior VP Sales in that they haven’t achieved all the things required of a VP Sales. However, they have recent hands-on sales experience and will work proactively towards earning the VP Sales title.

The costs and risks of hiring people align with their experience/career stage. If you are confident that it’s time to scale, you can afford to hire a VP Sales who will bring in results. If you think you can scale a little, you can start with a Head of Sales at a lower cost, but they may not be able to help you as much. All in all, be sure to understand the tradeoffs of your decisions.

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