Hiring Your First Sales Professional

By August 20, 2015Sales, The Team
hiring first sales rep

You built your MVP, got it launched to the delight of some paying customers and just raised some seed funding to move to the next phase of your company’s evolution.  You and your co-founder have been doing all of the selling (closing deals) but neither of you has real experience as a sales professional, so you decide it’s time to hire one.  Easy, right?  Well, maybe not as easy as you think.

Forget the recruiting process for a moment and take a step back.  Should you first hire a lead development rep, sales rep, sales manager, or sales executive?  How will you compensate them in the early days?  How will you know if they are performing well?  Let’s explore further.

Setting the Stage

Every startup is different, which means the ideal approach to hiring and managing your first sales professional can’t be blindly prescribed, but rather is greatly influenced by factors such as the following:

  • What sales model is ideal for your company?  (ie – direct or indirect?  inside or field sales?)
  • How involved is a typical sales cycle?  (quick and light touch or long and really involved?)
  • Do you already have a CRM system in place and with someone that knows how to administer it?
  • Are any of the company founders experienced at sales or sales management, even if that won’t be their primary role long-term?
  • How much funding do you have and how much are you prepared to spend on this role?
  • How mature is your marketing function, specifically demand generation?

Answers to the above questions will give a snapshot assessment about the company’s existing maturity level for the new sales function.

What Role Should You Hire First?

Before describing three different approaches you can take, I have to point out some things many founders don’t realize.  First, they have to close the first deals.  Even if they don’t have ninja selling skills, they understand the product and its value proposition better than anyone.  Second, if they can’t sell deals, it is unlikely a trained sales professional is going to yield a very different result.  Third, the founders stand to learn a ton from these sales interactions, including the ones that don’t lead to a closed sale.

After closing enough deals themselves in order to get to a point of raising money and being able to hire a sales professional, they might be thinking they’re pretty good “at this sales thing”.  Not so quick.

What they often don’t realize is they have magical powers that can redirect any and all company resources or commission any needed product changes in order to win a deal.  The sales professional you hire won’t have those magical powers and shouldn’t.  You’re hiring them to define and implement a repeatable sales process and methodology that will allow the company to rapidly grow.  Your prior focus was on closing a deal while their focus will be on closing many deals.

To understand this phenomenon better, read my article titled “You’re Not as Good at Sales as You Think

The “Lean” Approach

At the moment you conclude you’re ready to hire your first sales professional, there is probably still a lot to be learned and validated regarding your ideal sales model and sales process.  This goes back to the list of assessment questions above.  You might get lucky and have a particular business type that always calls for a specific sales model, but for startups that are innovating/disrupting existing markets or creating new ones, that will not be the case.  Below are a few things that you might still be trying to figure out:

  • What is the average deal size?
  • What is the typical sales cycle?
  • How complex is the value proposition?
  • How much hand-holding will be needed during customer trials?
  • Which buyer persona(s) should be targeted?
  • How much competition will be encountered and from whom?
  • Is the pricing strategy correct?

For all of these you must have a starting theory that you can test and hopefully validate.  But before achieving some validation, do you really want to spend a lot of your newly raised funds on a sales executive or even a highly experienced and successful sales rep?  Maybe not, they cost a lot of money.  And learning later that you took the wrong approach or hired someone with the wrong background is excruciatingly painful.

The “lean” approach calls for you as a founder to keep closing the deals but to insert one or more entry-level sales and sales support functions to help you be more efficient while also enabling you to continue the needed validation from the list above.  Then, once you can answer more of the questions with reasonable certainty, continue with whatever sales-related hiring best supports your findings.

What do I mean by “lean approach”?  Below is a common sequence that is implemented over time:

  1. Hire a Web Chat Rep
    Web chat is a fabulous utility for early learning.  Think about it for a second.  Interested prospects somehow find your website and start consuming your messaging and content.  Either prompted or unprompted, they engage in a web chat with your rep.  That engagement reveals common questions, objections and misunderstandings.  In fact, your web chat rep should specifically be trained to gather this information and identify patterns they can pass on to you and the rest of the team.  Web chat reps are typically the lowest compensated of any type of sales professional and you can often start them off in a part-time role until your web traffic justifies something full-time.
  2. Add Sales Development Responsibilities to the Web Chat Rep, or Possibly Hire a Dedicated Sales Development Rep (SDR)
    The decision to hire a second position versus simply adding more responsibilities to the Web Chat Rep is partly driven by workload and partly by available budget.  An SDR (sometimes called a lead development rep or LDR) is more proactive in their approach to identifying and engaging prospects for your offering.  They conduct a mix of outbound activities (sending emails or making phone calls against a list) and inbound activities (responding to contact requests made through your website or from a trade show you attended).  The SDR function requires more selling skills than a Web Chat Rep, but still offers great opportunities for validated learning and that should be clear in their job assignment.  SDR’s are more expensive than Web Chat Reps but considerably less expensive than a quota-carrying sales rep or sales manager.
  3. Hire a Sales Professional, Sales Manager or Sales Executive
    The trade-off between these three options is discussed further below.  The main argument I’m making in The Lean Approach is that a seasoned professional/manager/executive shouldn’t be hired until you actually know what type to get, based on your confirmed sales model and process.

Adding to the Executive Team First

Hiring a seasoned sales executive could actually be the right first move for your company.  The most common reason for this is when the other founders have little business experience and they and/or their investors strongly desire a seasoned executive to join the team.  That new executive doesn’t have to represent the sales function, but it’s certainly a possibility to consider.  In fact, in the early startup days, all executives wear multiple hats.  So this sales executive is probably also responsible for marketing, HR, refilling the refrigerator, and taking out the trash.  The main point is that they serve as an experienced executive on the management team.

The second most common reason to hire a sales executive first is when the average deal size is large ($100K or more), the product offering is at least somewhat complex, or the primary target market is large enterprises.  The sales model for such a company is almost certainly direct sales with sales reps in the field.

Hiring a seasoned sales executive first allows them to immediately put focus on establishing a sales process (stages and flow) and a sales methodology (how your sales team manages and influences the sales cycle).  This will lead to implementing sales support tools and sales-related metrics and KPI’s.

For more insights into the nuances of selling to large enterprises, read my article titled “Intro to Enterprise Sales

Side note:  If there’s great value from having a seasoned sales executive on the team but you absolutely can’t afford it, consider instead bringing on an Advisor with lots of experience in sales.  Specifically the type of sales you envision for your sales model (ie – direct vs indirect and/or inside versus field).  For equity-only compensation they won’t be able to do a lot of productive work but they can at least help you shape the right sales model, hire the best talent and double-check your proposed sales compensation, tools and processes.

If you do hire the sales executive first, it should be clear that they also wear the hat of the only sales rep.  In other words, you as a founder are no longer primarily responsible for closing deals – they are.  That doesn’t mean you don’t go on sales calls anymore.  My main point is that you can’t afford to hire a sales executive that doesn’t also close deals and do everything else sales-related.  For a while, they will effectively be the “sales department” and need to understand that from the beginning – especially if they’ve never worked for a startup.  I’ve seen lots of sales execs join a startup thinking they’re going to love going back to closing deals, but quick remember how much of a grind it is.  As a result, they quickly request to hire one or more sales reps that you can’t afford.

Hiring a Trained Killer First

Hiring an experienced quota-carrying sales rep or sales manager first is viable alternative to consider.  The trained professional will know how to close deals and will have enough close engagement with prospects and customers to assist with early learning and validation, which can be passed on to the rest of the company.

The trained professional won’t have the time or skills to implement a sound sales process and methodology.  They’ll just start selling and trying to make money, which can be great if you’ve already identified opportunities to keep them busy.  But if you don’t support them with continued marketing activities (demand generation, sales tools, etc), they will end up struggling and if they aren’t making money they won’t stay very long.

If you decide to hire a sales manager first, it also means they’ll need to close deals in the beginning.  But you might find that they are also able to start putting some process and methodology into place, in preparation for hiring some quota-carrying sales reps in the future – once the budget supports it.  Taking this concept further and hiring a sales director first sits somewhere in between hiring a sales rep and a sales executive.  You’ll want to double-confirm they understand they need to close deals and that it will be months (maybe quarters) before you’ll be able to add some sales reps underneath them.

What About Sales Compensation?

Most startup founders have not held a sales or sales management position and don’t even know where to start when it comes to setting a sales compensation plan.  For more advice and tools to help with this, see my related article titled “5 Golden Rules for Setting Sales Compensation Plans” and “Documenting Your Sales Compensation Plan“.   But the concepts described in the aforementioned articles don’t address the challenges of early stage startups that don’t have much cash to use for sales compensation and instead want to use equity to offset a “below market” cash offer.

The biggest challenge I find with offering sales professionals (LDR, inside sales, field sales, sales manager) a “below market” cash compensation in exchange for extra equity is that the best sales professionals are money hungry in a near-term and immediate way.  Their personality is optimized for killing the prey and eating what they kill.  They don’t usually like deferred compensation or iffy chances of making a lot of money.  They want to do ABC and know they will get XYZ in return.  I’m not suggesting you give up on the idea to compensate your first sales professional in a similar manner as you do your other very early employees (less cash, more equity), just be aware of this issue going into it.  See my related article titled “Compensating Your First Employees When You Are Cash Poor” for more insights and advice.

Also notice that I didn’t include the sales executive in the list.  That’s because there’s at least some chance you’ll find a seasoned executive that is ready to “swing for the fence” with a bunch of equity.  Maybe it’s because they’ve already made some money from an exit or maybe they had some great earnings years in sales and are ready to take “below market” cash compensation in exchange for something potentially really big in the end.

Assessing Performance

If you only have one sales professional, how do you know they are performing well?  I’m not referring to a Web Chat Rep or LDR but rather some form of quota-carrying sales rep or sales manager.  Let’s say they achieved less than 70% of their target the last two sales periods in a row.  Is it because they are ineffective in their sales skills or is it because of one or more of the following reasons:

  • Not enough leads to pursue or poor quality leads
  • The product is unstable or is missing critical features needed to close deals
  • The pricing is wrong
  • The competition is much stronger than expected

One thing is certain.  Your sales professional will be giving you these reasons whether they are true or not.  How do you know?  With just one sales professional, it will be very hard to determine the root cause of their poor performance.  My friend and Capital Factory colleague, Mikey Trafton, has learned that having 2 or 3 sales professionals from the beginning makes a huge difference in this regard.  Assuming you’re at least half decent at hiring sales professionals, if both/all of them are underperforming versus the targets that were set, either the targets are simply too aggressive or (more likely) something from the list above is causing the problem.  If, instead, one of the sales reps is performing well and the other(s) aren’t, then it is easier to conclude the other sales rep(s) aren’t of the caliber needed.

I realize hiring 2 or 3 sales professionals means double/triple the cost but at least be aware of the dilemma of only having one when it comes to assessing their performance.


The penalties for hiring the wrong first sales professional can be very damaging and distracting.  This relates to hiring the wrong role, skill, level or timing/sequence.  Your revenue engine depends on getting this at least mostly right from the beginning.  If it doesn’t seem to be working, don’t convince yourself that trying harder or waiting longer is going to fix it.  It rarely does and your cash is burning every week.  Also remember that the “fixing” might not lie with the sales function but rather elsewhere.

Related Reading

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