Building a World Class Technical Sales Organization at a Startup

A few years ago, an ebullient Jason Binder dialed me up about a startup named Delphix.  A few weeks later, I began a journey with a truly compelling technology that has brought me to manage a worldwide team .  And, I’ve learned a few things about what it takes to build a world class technical sales team at a startup:


Managing Yourself


Play your position: First Officer, Prizefighter Coach, or Fact Checker.  Sometimes the salesperson needs a first officer to understand the problem in depth, provide cogent, compelling advice, and execute a strategy flawlessly.  Sometimes she needs a prizefighter coach to arm them with facts, figures and knowledge to counter head blows and give a nice uppercut.  And sometimes, she needs a fact checker to keep her honest on product capabilities and tease out deal-killing gotchas.


Think like a CEO, not an Engineer.  Engineers are great problem solvers.  But, not all engineers successfully cross the divide from engineer to technical salesperson.  The successful ones I’ve seen are problem focused (focused on the customer’s problem not their solution), think expansively (consider and keep considering a wide arena of possible solutions), and know it’s not about them: they don’t need to be the smartest person in the room, but they strive to be the most valuable.


Qualify your time  just like your deals.  The funnel is always full, so the issue isn’t what to do but instead what not to do.  I could say yes to every request, but I would certainly never sleep and do many things poorly instead of a few well.  When I see a technical salesperson comfortably telling a peer or a customer “No” or “Wait”, I know they’ve qualified well, and have solved their own value equation.


As a manager, I prefer it when a technical salesperson is shared across many opportunities because it forces the qualification exercise all the time, and that gets us to No faster so we can spend more time on Yes.


You will fail to scale if you can’t scale yourself.  At a startup, scaling is about letting control go.  First, learn to manage yourself.  Second, when you are promoted, figure out how to scale and handoff what you used to do, transition yourself from player to coach, and build a skill set targeted at what you would want a manager to do for you.  At a startup if you’re not growing, you’re failing.  So, startups must always be industrializing through specialization, standardization, and harmonization.


Embrace the Negotiation.  Life is a negotiation, and the better your counterpart is - the better you have to be.  If you don’t understand and can’t articulate the value you bring, you will lose.  I’ve learned there’s almost always a way for both sides to win if you keep at it.  And, as the CEO of Delphix once told me “you’re always negotiating.”


Don’t just know it; Own it.  You can take all of the training in the world.  But that won’t replace taking the story you want to tell and being able to talk about that story in your own words and your own way.  Ownership leads to confidence.  Confidence leads to success.


Be multilingual.  In the software industry, pre-sales is about the intersection of technology and business acumen.  Success is often predicated on being fluent in both languages, tailoring your conversation to your audience, and moving the conversation between the two as appropriate.


Managing the Sale


The two most important questions are Why? and So What?  Your understanding can never be hardened enough.  I’ve had five different people tell me the Economic Buyer was, and found out they were all just plain wrong.  I’ve confirmed every POV metric with 6 teams and still had my champion tell their boss they have no idea what I am talking about.  So, I’ve embraced the ideals of an investigative reporter:

  1. Keep asking, “Why?”  Don’t be satisfied with the first answer, first person or first line of business. Ask 5 times!

  2. Get 3 sources.

  3. Be curious and willfully ignorant all the time: Ask open-ended, non-leading questions.

  4. Put the elephant on the table.  Ask the customer hard questions, “Why won’t you do this deal?”, “Do you believe this is the right answer for your problem?”.

  5. Be politely but eternally skeptical. Tell the customer, “I don’t believe it.”

  6. Understand motivations: Interest is different than investment.

When you are convincing the customer that a solution is right for them, and they listen, you have interest.  Whey they convince you that the solution is right for them, they are invested and a deal is close. (Thanks to Dave Krygoswski, Challenger Sale Adherent Extraordinaire)


Get to the truth, don’t cover it up.  Getting to the truth requires asking hard questions.  Most salespeople think their success rides on that, but it’s the customer who suffers when you’re not willing, ready and able to ask them hard questions.  No one wants to waste time on a product that doesn’t solve a real problem, proving that a product solves the wrong problem, and (except for science experiments) customers don’t want to invest time to solve a problem for which they’re unwilling to pay for a solution. (Thanks to Kevin Mosher and Jeff Zeisler)


Being a Leader


Lead by example.  When the folks on your team know that you’re willing to do what you ask them to do, and that you’ve suffered the same mind-numbing death march that they’re in, they know you have both sympathy and empathy and that you will be a brother in their adversity.


Show them you care.  Everyone has dreams and aspirations.  Everyone has trouble and conflict.  But in every case, everyone needs an advocate.  Everyone needs a leader who will take them seriously, do the best for them, help them navigate perilous waters, reward where possible, coach when necessary, and showcase their skills and accomplishments.  I know it because that’s what I want, too.


Thrive on Strength. Some people prefer to be challenged.  Some people see any challenge as a threat.  I find the best people thrive on challenge, and seek challenges to thrive on.  I believe that only the weak are threatened by strength.


Let them take credit first.   Give them bluebirds.  Help them out and then let them put their name to it.  Find that valuable thing that they would love to do but just don’t have the bandwidth and push them 80% of the way there.


Everything is always in flux.  One of my mentors told this to me to help me realize that your situation can always be changed because the situation around you is always changing.  It’s up to you to take advantage of that change. (Thanks to John Linehan)


Building Teams


Hiring is just another sale.  A startup asks very bright people to risk much for the promise of a payoff 5 or 10 years down the road.  A great candidate knows the risk of a startup, and is interested, not just shopping.  Just like in a sale, I’m not interested in being someone’s checkbox.  So, I spend a lot of time helping them see the value of the company, the potential for growth, and their potential in their role.


Not everyone has to be at the same level.  At the beginning in a startup, you need Top Gun because you don’t have time to train or build the farm league.  But, as you specialize and industrialize, you can bring on folks with less experience and let them be led by Top Gun.  The struggle is to keep evolving and improving the On-boarding, Mentoring, Training, Buddying, and peer support processes so that as the company industrializes processes and tools, the culture can industrialize all of the best practices and behaviors that Top Gun has so that the next generation of war fighters is prepared.


The winning formula for promoting managers is: competence plus charisma. You don’t always get both.  But, the first question to ask yourself is – can this person do the job?  Managing in a sales organization is a lot more about psychology and presence than it is about knowledge.  When you’re promoting someone to manager, you want to know that they can navigate the perilous waters.  Then, the second question to ask yourself is – can we live with their personality?  (Thanks to Kevin Mosher)


You can’t save everybody.  Some people you hire either won’t get the job done or will be unwilling to do the hard work to change themselves to be ready to get it done.  Sales is the tip of the spear.  A manager’s job is to do everything you can to make someone successful until it’s clear that they won’t do that for themselves.  (Thanks to Jeff Zeisler and Chris Fuller)


Delphix has assembled a team of the finest engineers in Silicon Valley.  We’re delivering a product with enormous power, simplicity, and impact.  Our growth has been legendary, our prospects are enormous, our position in the market is powerful, our technology is solid, and our customers are the leaders in their markets.  We’re building a giant software company based on a real opportunity with a solution that works and works well.  It’s the best place I’ve ever worked.  And, after a few years in, I’m more bullish than ever about Delphix.



Woody Evans is currently Vice President, Global PreSales at Delphix.

Connect with Woody on LinkedIn.

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