Impact Engine convened a group of industry-leading CEOs and sales experts at our 2019 Portfolio Summit and they offered up their pro tips on how to kick your sales into hyperdrive. Our portfolio companies were treated to a master class with some of the best in the business on a wide variety of sales-related topics. Below is a recap of the Portfolio Summit’s key takeaways.

Sales Hiring

During his career at LinkedIn, Mike Gamson (now the CEO of Relativity) had the rare opportunity to build a sales team from zero up to full maturation, which in the case of LinkedIn meant over 6,000 sales employees. Along the way, he learned a lot about how to develop an effective process for hiring salespeople while also creating the right company culture in an organization that began to experience rocket-like growth trajectory.

Setting the right culture

One of the first things he did after he started running sales at LinkedIn was to put together a list of traits or values that he wanted the first sales team to embody. The list included things like: bring humility to work, no jerks, and be intellectually curious. It’s important to stay true to these core values. Mike referred to one instance where he had hired someone who was productive and brought in deals, but proved to be a poor fit for the team culture. The individual didn’t uphold the team values, and had already violated some of their guidelines. Mike had to make an important decision — was he prepared to hire and fire people for the sake of culture? Ultimately, he decided to put culture first and bet that the big stuff matters, even if it meant he had to take on short-term professional risk in order to fix things. While the company’s short-term production took a hit when that person was fired, the long-term gain in production from that story set the tone for the rest of the team that over time, far surpassed the initial trough in productivity.

Diversity & Inclusion

When asked to reflect back on his biggest failure during this high-growth phase at LinkedIn, Mike pointed to the topic of diversity and inclusion. He felt that the organization could have recognized the lack of diversity sooner, which would have allowed them to address it earlier on. LinkedIn would go on to spend thousands of hours to make improvements and with the help of a group of senior women at the firm, they successfully devised and implemented a strategic change plan. Now LinkedIn has 50/50 women parity including senior positions. But looking back, Mike said it would have been far less work if he had the correct process in place from the beginning instead of having to fix it later on.

Be honest with what you have

From a product perspective, Mike believes there are two types of companies: those with differentiated products and those with commoditized products. The type of product you have will dictate the type of salespeople you should be hiring. When you have a differentiated product, you should actively seek out salespeople who are intellectually curious. They need to believe in your product and have a passion for the benefit that accrues for their customers. With a commodity product, it’s a race to the bottom on price. A salesperson better suited to selling differentiated products will not only cost more, but they will also find selling commoditized products uninspiring.

SaaS: Salesperson as a Scientist

Mike’s background prior to sales was as a product marketer, which may play a role in how he wants his salespeople to operate. He prefers that they take a scientific and thesis-driven approach to their interactions with the customer. Mike refers to this as Salesperson as a Scientist. He encourages them to constantly observe and record data on the customer’s experience with the product and use that information to develop a hypothesis about what changes they should make to the product rather than running to tell the product team every time a customer asks for a new feature.

Where to hunt for talent

Mike constantly looks at other organizations to try and identify companies that: a) have established a work culture that he admires, b) provide training to new hires that are extremely applicable at his company, and c) produces inquisitive people who ask great questions. Once he identifies these organizations, he systematically farms new hires from them.

How CEO’s can help their Head of Sales

Sam Yagan has been CEO of a slew of extremely successful D2C tech companies including SparkNotes, OKCupid, and the Match Group. But he had no experience with enterprise sales when he became the CEO of ShopRunner. It was a struggle at first to find the right fit for their Head of Sales. He went through multiple people early on that didn’t work out and their headhunter was constantly trying to force him to settle for candidates that didn’t check off all the boxes or weren’t a fit. For example, one candidate had a great rolodex of key players in the industry but was better suited to selling a mature product, which wasn’t ShopRunner’s world. Eventually he was able to land Chris Ladd, who has spent over 20 years working his way up the ranks at various retail companies. He had managed up to $1.4B P&L’s and as many as 4,000 employees. Chris turned out to be a perfect complement to Sam’s strengths and together they have developed a great multi-pronged approach to closing big enterprise deals.

Multi-threading through the organization is key

At ShopRunner, Chris and Sam are constantly chasing after large deals that have long sales cycles. Their game plan is to take a multi-pronged approach to developing and eventually closing new deals. They refer to this joint approach as multi-threading. Sam’s role is to share the vision, Chris brings the industry knowledge and retailer perspective, while the rep actually has to work out the details with their counterpart to get the deal done. By engaging the customer at multiple points along the org chart in a complementary fashion, they are able to build in redundancy to the sales process and get to a “yes” in a more efficient, effective manner. Multi-threading allows you to keep the deal alive and on track. It also allows the sales teams to leverage the CEO as a facilitator or unlock deals that are stuck. It isn’t necessarily about closing today — it’s about relationship building. It’s the entrepreneur’s responsibility to build trust with the most senior person you can find on the client side, which takes time. As a result, Chris will often coach his sales team to manage expectations around the sales cycle.

Scarcity is your friend

If you’re selling ahead of a new product, scarcity can be an effective tactic. If I can’t have you, I want you more. Behavioral science backs this up. When you chase after a sale, people become defensive so you need to defuse that tendency. Holding back can oftentimes create demand. Offering only a limited number of slots for the launch can become an advantage and will help manage the timing of onboarding clients.

Sales Tactics

As the CEO of Jellyvision, Amanda Lannert has been at the helm of one of Chicago’s fastest growing tech companies. The company has added about 100 employees a year while remaining cash flow positive during a recent period of rapid expansion. During this growth period, Jellyvision won numerous awards for its outstanding culture. More than 1,500 companies and 18 million employees in total now use Jellyvision’s software, ALEX, to choose the best benefit plan for their needs.

User experience design is the linchpin to everything Jellyvision does. Their journey has led them to believe that there are three fundamental truths of selling: a) everything is marketing, b) show that you listen and care, and c) we are all human.

Everything is Marketing

Every customer touch point is an opportunity to make an impression and build your brand. Amanda’s email auto-response to me as we were hammering out the details for her presentation at our Portfolio Summit is a wonderful example of making the most of any and every engagement to show off your brand. See the screenshot below:

Show That You Listen and Care

Build a culture around capturing all the finer details about a client, which Amanda refers to as instances of humanity, and calling on that. Run towards fires and solve problems because they will feel cared for and as a result will become your biggest evangelist. Jellyvision will often perform what Amanda calls “wild acts of romance”. For example, the account management team sends out hand-woven friendship bracelets for customers to thank them for their trust after they send over sensitive employee information. They also deliver Open-Enrollment Survival Kits to clients acknowledging the busiest time of their client’s year.

We Are All Human

Companies don’t buy from companies, people buy from people. Don’t get hamstrung on titles; you’re selling to risk takers or innovative buyers regardless of rank. Don’t be boring! Amanda cautions against underestimating how bored people are in their everyday lives. Jellyvision often uses humor to break down what can be a pretty stressful topic for their end use. But humor isn’t the only approach that works. The opposite of being boring is not to be funny — it’s to be interesting. Be interesting and you’ll be surprised out how that draws people out. How can you out-teach, out-joke…out-whatever your competition?

Lessons Learned about Startup Sales

Jellyvision’s best account reps have been the ones that are highly coachable, intrinsically motivated, and detail-oriented. Before you begin ramping up AE’s, Amanda recommends that you prepare first by defining the ideal customer profile, the buyer personas, and the key problems that they are expected to solve. A sales messaging cheat sheet is another great tool to provide. This all requires a relentless focus on process, because persistence pays off. Their data suggests that 80% of deals require at least 5 touches in order to close.

Sales Pitch and Messaging

Craig Wortmann wears many hats, but the common thread that runs through all of them is sales. As the CEO and Founder of Sales Engine, Craig helps companies improve their sales results. Craig Wortmann is a Clinical Professor of Innovation & Entrepreneurship in the Kellogg Innovation and Entrepreneurship Initiative (KIEI) and founder and executive director of the Kellogg Sales Institute. Craig is also an Operating Partner at Pritzker Group Venture Capital, where he advises portfolio companies on sales. Craig gave some expert guidance on how to message effectively and also offered some ways you can step up your networking game.

Our team is very grateful to have a network of subject matter experts who are committed to supporting Impact Engine’s entrepreneurs and their growing companies. We want to thank Craig Wortmann, Mike Gamson, Sam Yagan, Chris Ladd, and Amanda Lannert for generously contributing their time to our Portfolio Summit, and enabling us to share learnings with the greater Impact Engine community.

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