Your First Sales Hire Should be Senior

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One of the most important jobs for the Founder/CEO of an early stage startup is selling. We are talking to prospects, pitching the solution, gathering feedback, closing deals, and building the foundation of a sales process. When we start to see early success, our natural inclination is “This is working! Yes! If only we just could clone me so we could go faster…”

It’s at this point in the story where many founders make a critical mistake – a mistake I have personally made over and over again. We hire the “business hacker” – a hungry, ambitious, inexperienced person who we believe we can train in how to pitch, how to do cold outreach, and if they are good, scale from individual contributor to our future sales leader. We imagine that they will reduce our workload and enable us to sell more. Perhaps this person has some previous experience as a sales rep, but has never built a sales team or process from scratch themselves. Or, this person may have aspirations to be a founder – i.e., the “clone” that the CEO was hoping for.

While this strategy may sound good in theory, it rarely works. Here are the problems:

You aren’t as good at sales as you think

There may be nobody more qualified to pitch an early vision, garner excitement, and convince early adopters to buy into the cause than a Founder/CEO. In the earliest days, we are the best people to demonstrate momentum, and then attract others to join the team. However, there is a big difference between early adopter selling, and building a repeatable, predictable, scalable sales process.

Sales is both an art, science and skillset that just like anything else, gets better with practice. From handling sales objections, navigating complex enterprise org structures, to crafting effective sales commission compensation plans, most Founder/CEOs can “fake it until we make it” as sales people, but would probably end up on a performance improvement plan if we were held accountable to carrying a quota.

Sales reps need a lot of coaching to be effective

Sales is one of the most coaching-intensive functions of a company. There are a plethora of products designed to support sales coaching, from call recording software like Gong to (shameless plug) personality insights tools like Crystal. Being able to effectively coach sales reps is highly unique to the product and sales process they are working in, and is something that, just like the rest of sales, takes lots of practice and acquired skill. Even if you are able to ramp up on sales coaching, it will take up an exceptional amount of your time if you want your reps to be effective.

Being a functional leader makes it hard to also be the CEO

Hiring the business hacker (i.e. the “CEO clone”) requires training them up to be as effective as you are. The more time you are spending managing and training that first sales person, the less time you can zoom out to actually be the CEO (whether that means other leadership hiring, culture, vision, strategy, etc). The business hacker path keeps you tethered to the sales organization as the de facto Head of Sales until the person you hired can scale into a leader, which unfortunately is much less likely with someone that you are training from scratch.

When there are problems, it’ll be hard to diagnose what is wrong

In an early stage startup, so many things could throw a wrench in your team’s ability to sell effectively – lack of product market fit, not enough marketing, pricing/business model problems, and more. If you have someone with minimal sales experience in the role, when they inevitably struggle, it will be unclear why… is it because your product is just not ready to be sold, or is it that your salesperson doesn’t know how to sell? If you want to move fast and efficiently, you need to eliminate that ambiguity.

A better way

After falling into this trap too many times, I finally got it right at Crystal when we brought on Jamison Newall as our VP Sales. Jamison had worked his way up from rep to team lead to sales manager and director of sales. He had worked in similar sized organizations that had a similar B2B SaaS business model, and scaled their revenue exactly to where we were hoping to get in the next few years.

We brought Jamison to Crystal with a clear mandate: on day 1, and perhaps for the foreseeable future, he would be an individual contributor. His role was to personally sell, learn as he goes, and write the initial playbook for our sales process. He would need to prove things out by closing the first several deals using that playbook. Once we see that the early process is repeatable with Jamison doing it himself, he can then start hiring a team and transitioning from an individual contributor to a player-coach as we scale.

Fast forward about 18 months since we first hired Jamison, and we’ve nearly doubled our revenue, built a sales team of 8 people and learned a tremendous amount about how to go to market with our product. The results speak for themselves, and it’s now abundantly clear that hiring someone with experience and having them sell personally, write the playbook, and then build the team has several benefits:

You know that if they fail, it’s not likely because they are bad at sales

This is the most important benefit – clarity on what is working and what isn’t. As I mentioned earlier, by hiring someone with deep sales experience, you can more likely eliminate the variable of “my sales person doesn’t know how to sell” if things aren’t working, and tweak other elements of the product, marketing, business model, sales structure, etc.

You move much faster

When you bring on a senior, experienced salesperson on day 1, they can immediately get to work. You will need to walk them through how you have demoed the product in the past, but they will quickly write their own script that will likely be superior to yours. Additionally, hiring someone to start as an individual contributor even though they have management experience means when it is time to build the team, they already know what to do, as opposed to learning on your time. A good rule of thumb is that your first sales hire should be teaching you the best practices of selling, not the other way around.

Your put the right structure in place early

Similar to other functions, there are many components of “infrastructure” that go into building a sales team and process, from your demo pitch script to how your CRM is organized. A more senior salesperson will come in understanding the best practices and immediately start putting the right tools in place. There are a lot of decisions to be made early that have a trickle down effect in the future; for example, the pipeline stages used to track deals in your CRM and calculate sales forecasts. Getting this right early on will save you plenty of headaches later.

You don’t have to repeat the recruiting process by yourself

Finally, if you hire a proven sales person first, and they are successful, they will be far more qualified than you to drive the hiring process of the first sales reps. They know what to look for, and the type of rep that would be most likely to perform well with your product, deal size and sales cycle. Recruiting takes a ton of time, and at a minimum with someone more experienced, you don’t have to lead that recruiting process yourself.

Considering the clear benefits, why do so many early Founder/CEOs make the mistake of hiring the business hacker instead? It often comes down to a few reasons:

Hiring a senior person is intimidating – it looks easier to hire a rep / business hacker

I won’t deny it – hiring someone more senior will be harder. They will be more difficult to find, more difficult to interview and assess their skillset, and a greater risk of injecting new (often strong) opinions into the team. Additionally, you need to find someone willing to take the risk of leaving a leadership role to temporarily be an individual contributor, and then build a team in the future. Not every salesperson will be willing to take that risk, but someone that does will also likely thrive in the chaos of a fast-moving startup. However, the reality is that hiring senior people across all of the functional areas of your business is an important skill that every startup CEO needs to develop. I outlined my interview process for senior hires here.

A senior sales person is more expensive

No doubt about it – in the short run, hiring the business hacker would be significantly less expensive, in both cash and equity. However, the old adage “you get what you pay for, sometimes less, never more” rings true here. As long as you structure your comp plan to be a healthy mix of base and variable (ideally 50% and 50% respectively), you are limiting your downside risk. Paying a higher base for someone who knows what they are doing and can teach you how to build a great sales organization is well worth the investment.

You are giving up more control

One of the appealing notions of the business hacker is that the Founder/CEO still controls the sales process, delegating some of the blocking and tackling to this new hire. However, if you acknowledge that someone more experienced would do a better job at building a sales process and leading the future team than you could, giving up that control is worth it (and even beneficial).

With that said, I am not suggesting you give up full control on day 1. To the contrary, any new hire, including someone senior, needs to prove themselves early on and build trust before you give them full autonomy. Trust is earned by delivering tangible results. As I mentioned with our VP Sales, Jamison, it was only after he proved he could sell effectively himself with the sales process he created that we allocated the budget to hiring a sales team around him.

Considering the pros and cons outlined above, after much trial and error I have learned that it is far better to bring on a Jamison-like senior person as your first sales hire, let them prove out the sales model and then build a team. You’ll save time, save money in the long run, and grow your company faster.

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