3 things to consider before you make your first sales hire.

It’s been said that “you have to get past the carcass of your first VP of Sales” before you’ll actually start selling. But personally, I think it’s irresponsible to accept that mindset.


Your salespeople are some of the greatest assets you have as a startup. They’re the front lines to your customers, and an amazing source of insight into how they think and more importantly what they need to scale your business to greatness.


But, they’re also the ones responsible for shaping the first impression your customers will have on your company and product too. And while ANY bad sales hire can be incredibly devastating for your entire company, the first is probably one of the most important ones you’ll ever make for that reason.


Studies have shown that first impressions are really hard to reverse. And my experience has proven that to be true as well in sales.


For example, I can think of one startup in particular that didn’t get it right on the first hire and is currently in a vicious cycle of churn, on their 4th VP, and has a tough road ahead of them thanks to a bad reputation in the marketplace as a result of their internal strife.


But scenarios like that CAN be avoided. And when I look at the reasons why startups don’t get this right, it’s usually due to:


  1. Not really knowing how to hire in the first place
  2. Not really knowing what skills they’re looking for
  3. Not really knowing what to expect from their first sales hire


This is something that keeps me up at night (and why I started ATP after 20 years in sales). So that said, here’s what you need to think about before you make your first sales hire to make sure you get it right…the first time.


How much selling have you done so far and what have you learned?


If you haven’t made an attempt at sales yet as a founder, it’s not necessarily a bad thing… but it is something to be aware of so that your expectations are correct.


Many founders who haven’t attempted to sell their products themselves aren’t aware of the challenges that sales people face when they’re starting from scratch. It’s one of the toughest things you can do, since nothing is defined and everything is basically a blank white board waiting to be filled.


(Side note: it’s also a valuable exercise to make sure you understand your marketplace and buyer journey to make any potential changes you wouldn’t otherwise realize before it’s too late)


So if your revenue is currently at zero and you haven’t embraced the sales side of your business yet, it’s not enough to just look for a candidate with big numbers or an impressive current employer – you need to prioritize finding someone with a track record of successfully building out a sales function that compliments your business above all else.


Sales people with the skills to do this are not easy to find, so make sure to do your due diligence. Ask the right questions and make sure their “why” is aligned with yours – they’ll need that extra intrinsic motivation when things get tough.


(Related: to learn more about how to do that, see this post on how to use a scorecard to define what you need from your first hire)


That said, if you have done some homework (and had some sales success already), your talent pool could get a little bigger. Here’s what I mean.


Do you have an established go-to market strategy?


It may be logical to think that you’re ready to hire someone to help you scale if you’ve had some success selling on your own. However, I wouldn’t jump to that conclusion right away – you need to make sure your go-to market strategy is well fleshed out and tested first.


That’s an entire article all by itself, so if you’re not sure how to do that, here are some words of wisdom that break it down for you.


Regarding testing, there’s not really any other way to do it other than get out in the marketplace and have conversations based on your go-to market strategy. The most important piece, LISTEN and iterate based on what you learn.


Again, it’s not a bad thing if you want to hire someone to do this. You just need to know that this isn’t something that just any sales person will be able to do WELL.


If you don’t have time to take that responsibility on as a founder, and have the funds to hire someone to do it for you, I say go for it. Just make sure the person you hire has the track record, drive, and “chops” to pull it off.


But, if you’ve done your homework and have an initial product-customer fit properly defined, your talent pool starts to grow and it might make sense to look at a go-getter instead. Most strong salespeople with solid experience and the right mindset can take a fleshed out playbook and go make it happen for you.


Still, you will want to make sure the person you hire is comfortable working in a new environment where things are fresh and will change constantly (i.e. have that conversation in the interview).


More importantly, this doesn’t mean you take a backseat and aren’t involved. To get this right, you’ll want to take a collaborative approach (not micro-manage) to keeping your finger on the pulse of what’s happening on the front lines and offering guidance and necessary support along the way.


And, that’s something else to consider when you’re making your first hire…


How much time do you have to manage a sales team?


As someone who is a startup founder myself along with my experience building and scaling sales teams, I know firsthand how much work it takes to get a revenue stream rolling. It’s not easy!


So depending on how much time you have to manage and build out a sales team/person, you might want to consider a hiring a someone (i.e. a sales leader) to do it for you.


There’s no clear cut answer on this one though. Each startup and their situation will be different, so make sure you understand yours clearly.


Again, maybe you’ve already received a substantial amount of funding, and have the cash to hire a sales leader to build out a team and strategy for you. That’s wonderful news! If you’re already at capacity and then some, this is a terrific step that makes a lot of sense.


Just make sure to hire someone who is comfortable getting their hands dirty selling up front, knows what it takes to be successful in your environment, and doesn’t expect a well developed strategy or want to play with dashboards (more on that in a second).


On the flip side, if you’re bootstrapping, finding a single go-getter to flesh out your strategy and get your revenue stream started so you can hire another salesperson (or sales leader) for you might be a better choice at first.


No wrong answer here. Totally up to you based on what’s best for YOUR business – I’ve seen it work both ways. But before you make a final decision, one other quick note about hiring a sales leader…


What a sales leader is usually responsible for…


Every sales leader’s (Head of Sales, Director of Sales, VP of Sales, etc.) role looks different depending on stage of growth for a startup. But predominantly, they do the following:


  1. Set the foundation: Process, strategy, collateral, etc
  2. Recruit
  3. Develop, mentor, coach
  4. Manage up to communicate realistic expectations


A true SVP of Sales or CRO is not usually someone who is going to go out and get their hands dirty (though some of the best I’ve ever met do just that). Typically, they play in the strategy and coaching world.


And a VP of sales is NOT CHEAP (think $300K – $400K OTE). So while it may seem to make sense to hire a VP or other sales leader right off the bat to build your team, it’s often overkill unless you’ve really got the cash and have done your homework (think “Indy car as your daily driver” kind of overkill).


I’m not going to reinvent the wheel with this one – many people have said this, and Jason Lemkin nails it here. To summarize, here’s what he recommends (I agree 100%):


Stages and types of VP Sales (sales leaders):


  • Revenue < $1M → “The Evangelist”: Someone who is going to get you rolling, VP or not
  • Revenue $1M–$10M → “Mr. Make it Repeatable”: A VP who can take your initial efforts and turn it into a repeatable process.
  • Revenue $10M–$40M — “Ms. Go Big”: A VP who can scale your process to absurdity
  • Revenue $40M+ — “Mr. Dashboards”: A VP who is thinking high level strategy


One last thing to note: make sure not to over inflate your titles. Hiring someone in as a sales person and then giving them an SVP title doesn’t give them or you room to grow. It usually does more harm than good.

The key takeaway…


You can nail your first hire no matter where you’re at in your sales process or whether you hire a sales leader or not, as long as you have your expectations set correctly on what you need them to do.


Sales people are not machines for hire to crank out revenue. Finding a product-customer fit is hard work, and if you haven’t already done that ahead of time, you need to make sure whomever you bring in has the ability to do that above all else.


Additionally, keep in mind the more work you do ahead of time to test the waters, the easier it will be to find a salesperson who can come in and get it right on the first try to grow the mess out of your business.


Remember, people who  have the skills to build out a sales function are not easy to find and throwing the spaghetti against the wall in the hopes it will stick absolutely hurt your business not help it.


What lessons have you learned along the way as you’ve hired your first sales person? Or if you have questions about making your first sales hire, what are they? Chime in below!


As always, thanks for reading!


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-Amy Volas