© 2019 by Chris Barbin. All right reserved.

  • Chris Barbin

10 Tips for Mastering Enterprise Sales from a Master


When it comes to hiring and working with sales leaders, there are a few who are exceptional, a few who are terrible, and many somewhere in-between. You always remember the bad ones because they leave scars -- costing market share, killing team morale, sometimes even getting the company into legal trouble. The mediocre sales leaders are, well, mediocre. But the exceptional ones are those who propel companies and create legends. These leaders not only keep the revenue growing but also help guide a company’s vision, investment strategy, and cement a culture.


I’ve been lucky enough in my career to work with a few exceptional sales leaders, but none more so than Matt Thompson, the current EVP of Worldwide Field Operations at Adobe.


Matt and I first worked together at Borland in 2003, where he was SVP of Worldwide Sales. I reported into him as head of Services. When I left Borland to start Appirio, he kindly agreed to be one of our independent board member where he provided me, a first-time CEO, with invaluable insight, counsel and friendship. Matt has been in sales for 35 years, and at Adobe for 12 of those years. His tenure there is impressive (the industry average for a sales leader is less than 2 years), but the change he helped guide over that 12 years is what’s most impressive.


Adobe looks very different now than when Matt started in 2007. Back then Adobe’s annual revenue was a little over $3B. At the end of FY18, it was $9B and the company is projecting further growth for 2019. That’s impressive growth on some very big numbers. Adobe’s product mix also looks very different. When Matt first started at Adobe, he describes the company then as “steady and predictable." At that time, Adobe sold packaged software to consumers and creative professionals, mainly through long-time reseller partners. It had an 18-month product cycle. Today, Adobe is leading the digital media and digital experience space, selling to individuals, SMBs and very large enterprises in more than 200 countries. It is has become a leader in cloud computing, selling the vast majority of products and services through a subscription model with updates being pushed more consistently.


Needless to say Matt knows his stuff, but one of the greatest things about him is his willingness to share that knowledge to help others. I recently hosted a Q&A with Matt on the topic of Enterprise Sales, as part of my work with GGV’s Founders + Leaders program (more on this program here).


Matt shared a ton of great advice in the Q&A for sales leaders and growth-stage CEOs who are on the hook to hire sales leaders. But to keep it simple, here are 10 of my favorite tips along with some of Matt’s most memorable quote.


1. People, not processes. When it comes to focus, time and investment, Matt recommends over-rotating on people - going deeper on background checks, waiting for the right culture fit, spending time for one-on-ones and development. “Execution mistakes are easier to fix, but when you make a people mistake there’s a higher business impact. Especially with a leader.”


2. Go deep with fewer partners. Many companies overextend themselves when it comes to channel partnerships. Matt suggests going deep with fewer, learning from that relationship and process, and then tweak, rinse and repeat.


3. Invest in your talent. For a small company, this could be getting the team together in-person on a regular basis. For a large company, it could investing in a field enablement function. It also means looking inside the company when promoting. “Motivating and rallying your sales team is as important as any customer meeting.”


4. International success = focus & scale. Expanding internationally isn’t easy but can pay off big if you execute well. Matt suggests starting first with a compatible market (for an American company, perhaps the UK and Australia), hiring a leader with some “juice” and giving that person the authority and scale to make decisions and move fast. “A complicated set of matrices will slow you down. You need scale to build a brand in that region, so don’t go in with one person. Ideally you want a 10 or 20 pack.


5. Beware regulated markets. When you sell into 200 countries and dozens of verticals, it’s tough to give advice on which markets to avoid but Matt urges caution when going after regulated markets.“Regulated markets have a completely different way of selling, and mistakes can be expensive.”


6. Customers follow product. If you want to create a customer-centric culture, Matt suggests starting with the product. If you start with a great product that provides great value to customers, everything will follow. Then you just need to focus on the wrapper.


7. Adapt models and incentives often. No matter its size, a company needs to be able to shift its sales models and incentives according to the business' goals, what products are strategic and what’s important to the brand. “At Adobe, we consistently adjust our model based on what we’re trying to accomplish.”


8. Make big bets. One of the most important traits in a sales leader is the ability to proactively make decisions. Those decisions might not be right every time, but if you have good judgement and the right data, you should be right at least 51% of the time. “I like to double or triple down on a bet when I feel something is ready for prime time. You can always undo a decision, you can’t undo not making one.”


9. No half-baked promotions. Often leaders will promote a good sales person into a management role but still leave them with a territory or quota to cover both bases. Matt cautions against this kind of hybrid promotion. Reps feel like they’re competing with their boss, and the new managers can’t focus on building and developing their team if they are still chasing deals.


10. Business by nature is imperfect. Nothing is perfect, no matter what size company you are. Whether you’re building your plan, setting quotas or servicing customers, there will always be challenges. “Leaders need to get their heads around this fact, know which problems they’re going to nail and then execute on their mission as best they possibly can.”