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High performance sales culture doesn’t just happen.  You have to be deliberate and consistent and communicate about it.

xamAt Xamarin, we built a sales team of 110 with a 5-star Glassdoor rating, less than 3% turnover, and we grew our business at an insane pace (triple, triple, double, double baby!) culminating in a tremendous exit when we were acquired by Microsoft for nearly $500M.  My role was Vice President of Sales Strategy and Enablement so people frequently ask me about our secret sauce.

As a builder of sales organizations, it’s tempting to talk about our amazing product-market fit, our incredible marketing machine, or our cutting edge lead-to-cash process. But the real secret to our success was our culture and the way we recruited, motivated, and developed our people. To build a high performance sales organization, you have to build a culture and environment that inspires people to bring their best every day.  Here are some challenges we faced and things we did that seemed to work.

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Coaching Challenges and Opportunities

Millennials and The Old Guard of B2B Sales. In organizations who serve both enterprise and prosumer customer segments, it’s important to get your mix of millennials and Old Guard just right.  These groups have a lot to learn from each other.  A good mix of these skills and personalities can do wonders for your sales effectiveness and team development!   You can read more detail in our post about The Complementarity of Old Guard and Millennial Sellers.

Over-Emphasizing Individual Performance.  Too much emphasis on the performance of individuals can lead executives to over invest in eagles (expensive, top performing sales professionals whose approaches are notoriously difficult to replicate) and sales hacking tricks.  These tend to mask underlying scalability issues and distract from optimizing the unit economics of the entire sales organization.  As volumes increase, the sales organization is simply not ready, and many companies miss their window for explosive growth.  My friend and mentor, Jacco van der Kooij describes this beautifully in his HBR article with Frank Cespedes, Hiring Star Salespeople Isn’t the Best Way to Grow.

The Compounding Effect of Culture.  High employee turnover on your sales team is expensive, not only due to costs associated with onboarding new hires but also because it hurts customer confidence and plants the seeds for churn.  Websites like Glassdoor are forums for employees past and present to share their experiences publicly for any prospective candidates or current employees to read.  Taken together, bad cultural experiences can compound employee turnover and make recruiting very difficult.

What Worked for Us


Lesson 1: Start with why.

I join places where I can do my life’s best work, so my teams can do their lives’ best work.  Simon Sinek explains it best in his TED Talk and book: Start With Why.  A tangible, crazy clear sense of purpose goes a long, long way toward creating unity and strength on your team.  With millennials, you need to build a sense of purpose into everything you do. 

Lesson 2: Build an awesome leadership team.

Your sales leadership team is the cornerstone of your sales culture and your first pod is the primus inter pares example for everyone who comes after.  Keeping your hiring bar extremely high for these groups may be the single most important element to shaping a winning culture.  Do. Not. Compromise. Hire for character, energy, intellectual horsepower, and cultural fit; train for skills and product knowledge.  Your sales leaders must be able to inspire and ‘helpfully manage’ millennials.

Lesson 3: Choose your words.

Words are powerful beyond measure, and the attitudes, tones, timing, and mediums by which they are delivered matters a lot.  Are we preaching FUD or FOMO?  Do we have a why or why not attitude toward suggestions?  As managers are we managing or are we helping?   Are we having a <serious> discussion, or a conversation or just talking about something?   When things get tough, do we become warmer/friendlier or harder/combative?

Lesson 4: Communicate about culture.

“The most important thing we sell is the fact that we care.”  Stephanie Schatz, Xamarin’s SVP of Sales and Customer Success said it to me during my first interview, she presented it (along with our other cultural epithets) to every new hire group who joined our team.  Our leadership team repeated our cultural tenets during our daily meetings, and we all used them as guiding principles when making decisions.  When you hire aggressively, new faces will fill your halls every day and you will need to communicate about culture to a degree that may seem completely absurd.  But keep doing it.  Here are some tenets we stood by and repeated regularly:

  1. We are here to do our lives’ best work.  (This is our moment, so bring your A-game!)
  2. Better every day.
  3. Be authentic, be helpful, be curious.
  4. A promise is a promise is a promise.
  5. Everybody needs to buy, but nobody wants to be sold to.
  6. Build strong personal relationships with your professional networks.
  7. Respect the right to be different. Help our customers (especially non-English speakers) feel comfortable.


Lesson 5: Be customer centric.

Being customer-centric begins with having an attitude toward helping customers be successful and earning your sales long after the deals close.  Map out how your customers are buying and build your sales organization and process to support that.  This is a BIG part of creating a purpose-driven sales team.  Are you proud of how you sell?

Lesson 6: Be generous.

When you have a base goal, a stretch goal, and a super-stretch goal for every month or quarter, you are constantly asking your team to perform better than they ever have before.  If you aren’t careful you will create burnout.  Designing your targets so that every individual can reach 120% creates a feeling of winning as a company AND as individuals.  Over time this ‘champions mentality’ sinks into people’s souls, and even your lowest performers rise dramatically.  At the end of a tough month or quarter, this ‘can do’ attitude is what motivates your team to dig deep and self-organize to work through weekends and pull 24-hour shifts until the job gets done.

Lesson 7: Team bonding: work hard, play hard together.

Finding common values (like healthiness), building work-plus-personal relationships, and tapping into competitive juices can create an environment for sellers to be the best versions of themselves.  At Xamarin, we stocked our kitchen with goodies, had lunch (and frequently dinner) catered every day, and we ate together at the same time.  We built fun into our sales floor layout with constant competitions on everything from ping pong to chess to pull-ups to ultimate frisbee to multi-player online games.  We became famous for our team planks, which we used as a way to boost energy (instead of coffee).  We had lots and lots of office dogs and a bike guy who kept us all rolling.  We took near daily walks up Coit Tower or around the block.  After quarter end, we would have organization-wide Awesome Days which were really awesome:  we’d start with a hike to the beach, play some football or soccer, and take busses to Sonoma for an afternoon in the wine country and a special dinner together.

Lesson 8: Career development and skill mastery.

Millennials want a clear career progression path marked by building skills as they go.  Initially they want to earn autonomy, then mastery marked by ~3-5 month ‘graduations’ to more senior levels.  Is this the gamification of career development?  Yes.  At Xamarin, we invested in formal training on things like Challenger, solution selling and presentation skills.  We had a very thorough onboarding process.  But we also adopted the mentality that development is a team sport so peers/mentors helped each other get better every day.

Lesson 9: Sales floor plan.

How you layout your sales floor matters.  In his book Blueprints for a SaaS Sales Organization, Jacco van der Kooij says it best, “A well-designed sales operations center can transform your business with improved communications.”  I couldn’t agree more.  At Xamarin, we kept as many people in one office location as possible.  We had multiple roles (SDR, CSM, AE, SEs) sitting near one another in an open floor plan that encouraged great communication.  We had call booths, meeting rooms, video-conference rooms, (and a storage closet) for private conversations or meetings.  Information and energy flow was constant.

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About SalesSmyth

We created SalesSmyth because we knew there had to be a better way for growth stage companies to build their sales organizations.  We’re sales leaders and consultants, so we’ve seen firsthand the effects of building a sales team by the seat of your pants: higher burn rates, lower valuations, and less control over the future of your company.  So we ask ourselves the question that drives us, “What can we do to help entrepreneurs build high performing sales teams that lead to explosive growth?”  We are on a mission to deliver torrents of revenue by designing, training and equipping sales organizations to do their very best work.

About The Author

Sam Henry is an entrepreneur and sales executive who gets fired up about bringing new businesses and world-changing software to market.  Sam is Managing Partner at SalesSmyth a management consulting firm who helps design, train and equip SaaS sales organizations.  Most recently, Sam was Vice President of Sales Strategy and Enablement for Xamarin (acquired by Microsoft) helping to bring world-class mobile solutions to developers in businesses everywhere.  In 2009, Sam co-founded Henry & Company, an angel investment firm that invests predominantly in professional services businesses and Colorado real estate providing capital and hands-on engagement to drive growth.  Prior to Xamarin, Sam spent fourteen years in various sales and marketing leadership roles at Microsoft. Sam lives in the mountains of Colorado with his dream girl and their four amazing kids.

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