Hiring · Sales

Have advice on hiring a first head of sales?


May 20th, 2015

I’m currently evaluating a role that I assume many on here hired - my first dedicated head of sales.  This has been written about extensively, with The Hard Thing About Hard Things sticking out in my mind as doing an excellent job.  Horowitz there lays out the question of hiring someone who can manage the group for the next year but may hit a ceiling soon vs a world class sales leader who may know how to manage a 300 person sales org but is wasted on the first five hires. With that challenge in mind, I’m starting to have conversations with pot’l VPs of Sales. My target market (institutional investors) is well established and currently served by existing dinosaurs, and based to a great degree on relationships. In that way, I think it’s analogous to ad tech a few years ago. 

Assuming you had the ability to recruit anyone, would you target the heads of sales for those orgs (late in their careers but national rolodex), or younger mid-level folks (less established ideals but much smaller and likely regional rolodex)?  Curious who the best ad tech rising companies targeted, in the early months and perhaps later if changes happened when scaling. Thanks! 

David Frankel Chief Marketing Officer | General Manager | FinTech Entrepreneur | Advisor

May 20th, 2015

Having managed and hired sales teams that provide services and technology to the institutional investment community for my entire career (both at startups and growing companies), I can tell you that you are selling into a difficult market to crack, particularly if you are creating a brand new solution or category.  Workflows are established, the clientele is extremely risk averse, and they are surprisingly slow to adopt innovation solutions.  As I say, in this space, it is "evolution" not "revolution."

What does that mean when you are hiring a head of sales? You need to be extremely careful about hiring someone (especially a higher priced, senior sales manager) that is "established" or has great "pedigree" or has worked at one of the big dinosaurs for a long time -- particularly if you have not yet figured out an established, repeatable value proposition, a tested pricing model, or know how to fill your pipeline with real opportunities. From my experience, the ambiguity, lack of established marketing presence, and lack of real cash earning potential (due to long and unpredictable sales cycles) for the head of sales makes these hires very risky on both sides (at a very high cost).  I've seen many a senior candidate that "looks great on paper" not work out because the realities of selling a new product into this space are more challenging than they are used to handling. They also become gun shy about trading on their reputation in their network to get traction for an untested product.

Unless you have cracked the code on your market fit and have shown that you are getting good traction with your positioning and pricing through closing deals on your own, then it might be a good time to hire the more senior manager, as their experience optimizing a pipeline can be extremely valuable.  Otherwise, I strongly suggest hiring someone who is hungry, fearless, open to ambiguity (both in marketing messaging and earnings potential), and entrepreneurial to partner with you until you figure out the right model.  If this is the stage you are in, you are less likely in need of efficient pipeline management and you more than likely need data points to establish a true sales model. That also means that right now, you are the head of sales and your hire is the sales rep that gets the meetings and does the deal execution.

Happy to connect offline if you would like to hear more specifics about some of my experiences.  Good luck!

Rob G

May 20th, 2015

Assuming you have no sales people on board yet and thus no one for this 'VP' to manage your critical path is to generate sales.  without sales there is no need for additional sales people and thus no need for a VP to manage them.   Also assuming your model is B2B enterprise ???.  You need someone who still remembers how to get their hands dirty.  My preference is always to hire natural 'athletes' (metaphorically) first and then look to their specific experience.  Good athletes can play a variety of roles, love to compete, love to win, know what teamwork means and most importantly can think on their feet (startup sales demands this). If you can find a natural athlete who is also a natural leader then that's your gold mine regardless of age and experience, although they must have some track record in your industry so this does not mean a complete rookie.  to use a football metaphor i'd hire a young Russell Wilson now and perhaps a Bret Favre later to grow the team around Wilson and to teach him how to lead. Too many sales managers and sales VPs have forgotten how to do the messy grunt work and you need that early on.  So i would say look for a younger, hungry sales athlete who has proven his/her skills in the trenches who has perhaps moved up to managing a small team or region and thus have some experience dealing with sales team dynamics, hiring, sales plans, comp plans, conflict resolution, contract negotiations, etc. I'd also look at those sales athletes who have not yet lead a team but believe they are ready to lead.  If it turns out they aren't the best leader then you can always hire that experienced VP later as you grow.  These experienced VPs can open bigger doors to bigger deals with their relationships and can help you mature and grow your sales team, but may not have the mindset to handle startup life in the early stages AND your company may not be ready for the larger, higher exposure deals these current VPs would bring in. 

Dan Ostroff Founder & CEO at Doogma Inc.

May 21st, 2015

Hi Ray,

There is good info here: http://www.saastr.com/how-to-hire-a-great-vp-sales-the-full-video-and-transcript/

Good Luck,


Bill Kelley

May 20th, 2015

In the startup world, your first hire is a "player/coach." Someone who can make sales, and as the team grows, consistenty outperforms the other sales people based on talent and hard work.

I think narrowing the search by looking for veteran sales VPs or mid-level sales people with leadership potential is a mistake. The startup environment is a tough one for many salespeople, and you need to find someone who is both a salesperson and entrepreneurial. That person can come from either environment. 

Certainly a pertinent Rolodex is huge, but if the holder of that Rolodex is used to a lot of sales support, you may be better off with a less-established but hungry sales leader.

Janis Machala Senior business executive and entrepreneur

May 20th, 2015

I highly suggest you read the Mark Leslie HBR piece on the Sales Learning Curve There's a very small population of sales execs who can do the 1st $5M or $10M in sales because they need to sell, scale, learn, etc. This article is the BEST piece out there on how this early sales phase works.

Dan Morris VP Sales at Zootly. Startup Sales Strategy Expert Building A B2B Sales Team In New York City.

May 20th, 2015

Hi Ray - this is a great question. I've built and run sales teams for three startup products, ranging from just me up to 47 people. The "scrappy" part is in my eyes the most fun, working out what works, why, and teaching it to others so they can succeed and increase the bottom line - it's the best win/win out there!

I think the most important characteristics to look for in your head of sales are fast industry and product learning, an element of data analysis (past performance and trends) and ability to connect the dots, then teach others. You're going to be working out a lot of sales challenges to get the first few clients, then the next X number of deals (depending on sales cycle) will show trends and more data for decision making.

This hire needs to be able to test and learn methods for you and report on what they did to win deals and why. You can then build processes to repeat best practice. Automating research and sales prospecting processes can definitely help once you know your conversion rates and times in each stage of the sales funnel.

Until you know for sure that you have enough database or market to fuel your reps, be wary of scaling too fast.

Happy to discuss in detail if it helps, feel free to message me directly.

David Telleen-Lawton Using Customer Discovery to mold innovative Master of Technology Management degree

May 20th, 2015

Ray, I do NOT have experience hiring a VP of Sales, but I’ve been one. I have also often been the first head of sales, usually as the first salesperson in an early startup. However, I feel strongly about some key elements as you decide on your head of sales. First of all, they need to be Consciously Competent. You’ve probably heard of that term. Basically, they should be able to articulate clearly their view of the selling process, what they feel will be key for yours (they better be asking a ton of questions of you and asking for facts to figure this out), and where else they’ve worked that has a similar model (and likely how they will tweek it to fit your company’s specifics). I see you’ve been a Director of Business Development, so you’ve probably seen your fair share of BS-ers in sales and BD land. If they BS at all, want you to think they already know all the answers, or do not ask a ton of questions about your process today, what works, current customers, how they were landed, etc., then back away quickly and keep looking. There are few things worse than switching out your head of sales because the one you have is a bum. Better to keep doing what you’re doing than to go through the pain of switching. Did I mention references, especially past customers and people who reported to your candidate? I know these are all basics; this position is NOT the one to cut any corners or rush a decision or chose someone because you need someone now and they’re the best you’ve seen so far. Of course industry contact knowledge is important, but only if it’s precisely in your target market to the same decision-makers. If it is, then find some of your customers or future customers that know this person and talk to them before you hire. I would hire someone that was weak on industry contact knowledge if everything else was stellar AND they explained to you how they would gain these contacts and provide an idea on how they have done that in the past. Good luck! DTL ============================ David Telleen-Lawton Technology Management Program Career Development Manager 805.453.6071 (mobile) DTL@TMP.ucsb.edu

Scott McGregor Advisor, co-founder, consultant and part time executive to Tech Start-ups. Based in Silicon Valley.

May 21st, 2015

I highly recommend you read Selling The Wheel by Howard Stevens and Jeff Cox. It is a fast read in the form of a business novel that covers the 4 different sales stages your company will go through while your market evolves, and why you need a different type of sales man and sales manager at each phase (so no do not hire the sales manager for future problems, he won't get you through the current challenges). I kept making the mistake of hiring late stage sales managers with big roladexes when I was still early stage with poor results. This book helped me choose appropriate sales people for my stage, and I recommend it to my coaching clients and advisees. Scott McGregor, Scott@soundfit.me, Sent from my iPhone

Julien Fruchier Founder at Republic of Change

May 20th, 2015

You're asking for advice on who to hire but you provide zero information about what you do (B2B? industry?), the role, the size of your organization or what your plans/projections are for the near to mid term (instrumental for a sales role). KInda challenging to provide any kind of constructive feedback without these salient points. 

Richard CSO Sales Process | Operational Optimization

May 20th, 2015

You may want to consider someone like me. 55 years old. Owned and Operated a Broker Dealer and Investment Advisory firm. Top sales professional. Trained salespeople and well trained in sales and sales systems. Currently unwinding role in start-up company. Let me know your thoughts. Thanks!