Top Takeaways from our High Alpha Customer Success Flight School

On Thursday, December 6th, Customer Success leaders from across the High Alpha portfolio joined us in Indianapolis for our annual Customer Success Flight School. The day covered a wide range of topics with leaders from across the country sharing their insights and takeaways. Below are a handful of takeaways from the day.

Customer Success Should Always Be at the Table

The day kicked-off with High Alpha Partner, Mike Fitzgerald, and Chief Customer Officer of MetaCX (High Alpha’s newest Studio Company), Dave Duke, sat down to talk about the relationship between venture capital and customer success leaders. A big emphasis from Mike as a former founder and now investor was that understanding different customer bases of investments is crucial and the best decisions can be made when Customer Success leaders are at the table. An early focus for High Alpha, according to Mike, has been on the Customer Success function and he believes this comes from the fact that the partners are all operators.

Consider How Your Company Measures Impact

Corey Kime, VP of Client Experience at Lessonly, shared the company’s unique learning impact framework that his team recently rolled out to scale on how much impact they are having with their clients. Lessonly sells a team learning software and this framework has been developed to follow a specific path of evaluation:

  • Learner engagement — are clients completing their training?
  • Training satisfaction — are you, learners, actually content with the training received?
  • Efficiencies gained — how is our software actually benefiting the customer?
  • Business line impact — how is our software impacting the customer’s business?

Developing a unified process for the Customer Success team to follow has allowed the Lessonly team to adopt a common language to speak, given additional purpose to conversations customer experience managers were having with their customers and pushed their customers to stretch their thinking of what success can mean. Along the way, the team has also learned that getting to the top of the maturity model was still very hard. Feedback loops developed with their customers and they have identified that reframing is difficult for a customer if their expectation isn’t aligned pre-sale.

Another big takeaway from Lessonly’s specific framework: don’t devalue the bottom of the model — not everyone will get be able to identify their business line impact. You have to get into the customers’ world and understand that if they are happy with an outcome that is different than how you would define success, that it is okay to readjust and adapt with them and define success differently based on how they are finding value from your product.

Start with the End-Goal in Mind

One of the most valuable parts of High Alpha Flight Schools is the opportunity to bring together leaders in a space for unique, intimate conversations. Courtney Shaffer Lovold, Rachel Rewerts, Tony Rhine, and Dave Duke participated in a panel discussion focused on managing enterprise accounts.

When managing big brands and big deals, there can sometimes be big egos that fall onto customer success teams. Managing these types of accounts has their own unique challenges. It starts with setting expectations. What are the expectations going into a meeting with this client? Start with the end goal for this client and work backward — What do they have? What tools do I have? Where do we want them to be because of our product? Understanding the end goal and as a leader, identifying this clear objective and articulating this purpose and value of an account allows your customer success team to focus on this and rally around this goal. Starting with the end goal in mind allows Customer Success teams to jump really deep really fast into accounts, to see where their customers are at and get a better understanding of a large, more complex client base.

Sales Challenges Should Drive Customer Success Alignment

A big miss that often occurs in a business can be a misalignment between the sales team and the customer success team. Doxly’s VP of Customer Success, Natalie Fedie, and Executive Chairman, Christopher Clapp, discussed how they use outcome engineering to ensure that their sales and customer success strategies are aligned.

From sales to implementation to customer success, you have to tailor what “efficiency” and “success” mean for your customers specifically. Early in the sales journey, the sales cycle has implications on how you can frame up a conversation about customer success. Showcasing that you care about your potential customer's goals for success in their own company allows you to better sell to meet their needs and ultimately smoothly hand-off the relationship to a Customer Success team with an aligned understanding of what is needed to maintain, and ultimately upsell or renew that customer. A great quote from the session was “Selling will help, but helping will sell.”

The Customer Experience Is Relevant to Everyone

To close out the day, Steve Sanchez, VP of Customer Success at Terminus, shared his thoughts on how Customer Success teams and Marketing teams as a whole should be thinking about customer marketing and the customer experience for existing customers. During this session, Abby Borden eloquently shared, “If you’re not marketing to your existing customers, someone else is.”

Flight Schools are an exclusive opportunity for our portfolio companies to come together to share learning and collaboration between companies, fully leveraging the benefits of the High Alpha network.

Look out for more High Alpha Flight Schools in 2019. In the meantime, you can learn more about High Alpha here or learn more about current job opportunities at High Alpha and our portfolio companies.


High Alpha is a venture studio pioneering a new model for entrepreneurship that unites company building and venture capital. To learn more, visit highalpha.com or subscribe to our newsletter.