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Hiring a Sales Leader after a Series A Round

While our firm has become synonymous with our very successful Product Practice, Martyn Bassett Associates was founded building sales teams that drive revenue for B2B SaaS companies.

Since our inception, we’ve been placing VP Sales candidates for some of the world's most innovative tech companies in martech, analytics, CX, ERP, financials, WHS, and banking software. In fact, 80% of our firm's clients have been venture-backed startups, many of them Seed or Series A backed.

When it comes to a Founder/CEO hiring a company's first VP Sales, we've learned a few lessons from the decisions we've seen many tech Founders make. In some cases, there have been some highly publicized lessons.

Based on all the lessons, failures, and successes we’ve seen over the last 20 years, we want to provide Series A Founders with some tips for building and hiring a software sales team.

(1) Big Company Titans

Often, when a Founder/CEO imagines the success of their business, they point to the titans of the industry as companies whose business models they admire and aspire to be 'one day.' For this reason, many Founders also get excited at the prospect of hiring a sales leader from one of these 'titans.' “Get me someone from Salesforce, Oracle, or Hubspot!" 

While we have seen some of those candidates become successful in early-stage companies, most are not. The old saying goes, "no one ever got fired for buying IBM" but the same could be said of any of these sales leaders at global enterprises. So ask yourself, how hard does an AE need to work to educate a prospect about who Salesforce is?

Now compare that to a Series A startup which most likely no one has heard of, doesn't yet have product-market fit and only has a couple of early customers who were funding the development of the product. It becomes a very different sales playing field. 

Choosing to hire your first sales leader requires more than just hiring a rockstar from a global brand. It requires looking for a candidate who has a track record of success from a similar stage business.

(2) Setting the Stage

Setting the stage for success requires making the right decision on who will champion the sales side of the house. This will free up Founders to come in as the closer or the subject matter expert, depending on the type of Founder and their superpower.

Look for sales candidates with the right past experiences - whose stories might sound like:

  • Hired by a Founder as the first formal salesperson but with the title of Head of Sales.
  • Pursued and won the company's first paying customers.
  • Grew ARR from $abc to $xyz over 3 years.

Or, if they do come from a scaleup, look for those hired as the first AE to open up a new market, define a new vertical, or take a net-new product into the market.

The key is to look for and qualify against the skills necessary to do something new, where there was no legacy coattails to ride upon. That profile of sales leader is often risk-tolerant, capable of working with few resources or support, and therefore has an increased likelihood of success.

(3) Player, Coach, or Player-Coach?

When hiring a venture-funded first-time sales leader, the first thing to determine is whether a player, coach or player-coach is needed before any decisions are made. 

The Player persona will be the easiest to hire of the three personas as individual contributors Sales Executives are the majority of the hiring market. Money plus unlimited opportunity with uncapped commissions will attract the risk-takers - especially if they already have market knowledge of a startup's buyer persona, shortening their ramp-up time.

The Coach persona is needed when a business plan and approved budget require someone to immediately join and build a team. Qualifying for experience in hiring and team building is essential. Would they know how to do it without a budget for service firms or internal recruiters? Would people follow them to a company? These are the essential questions to ask anyone coming in to lead the Head of Sales as a coach.

The Player-coach persona is always the toughest combination to find because how much player, how much coach? Some salespeople who are high-performance players make terrible coaches and vice versa. Positioning this type of role in the market is a delicate matter as some candidates perceive this as a company that wants it all but is not willing to spend to hire a "real" VP of Sales. While this can be true, often it’s because Series A startups simply don't have the budget, but this can also be an opportunity for someone young and hungry to get it and build up their skills. 

Hiring a Sales Leader for a Series A organization requires someone with a particular set of experiences and personality to tolerate risk and ambiguity. Before starting the interview process, take the time to hone in on the essential skills and experience necessary to get the organization from A to B (pun intended)

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