Sales Flight School 2018

On May 17th, Sales leaders from across the High Alpha portfolio gathered at Smash Social in Indianapolis for our first “Sales Flight School”.

30 + sales leaders from across the High Alpha portfolio gathered together for 4 content sessions and plenty of discussion and networking. Below are the key takeaways from our inaugural event.

Find, Evaluate, and Retain Your Talent

Derek Grant, VP of Commercial Sales at SalesLoft shared his expertise on hiring and retaining top talent for sales roles in your organization. Grant emphasized that the culture of your organization should be a focal point. By having well-defined company values and keeping those at the forefront of everything you do, you will attract and retain the best talent. SalesLoft focuses on its 5 core values.

  • Put Customers First
  • Glass Half Full
  • Team Over Self
  • Focus on Results
  • Bias Towards Action

These 5 values drive the internal, award-winning culture at SalesLoft and are integral to their process for attracting new talent, too. Grant was able to provide some hints on the best ways he has seen organizations find, evaluate, and retain talent.

Find the Right People Scalably & Affordably

Not only do you want to attract top talent, you want to do it in a way that ultimately invests back into your organization. Try and avoid external recruiters, and instead use internal resources such as an incentivized internal refferals program. A program that incentivies your current employees will keep them on the look out for top-talent in their networks and allow the best recruiting to happen naturally in social and professional circles your trusted employees are already connected with. Your current employees are the best informants on culture and will better draw in great talent that fits in with your organization. Another internal-driven recruitment talent is hosting talent events such as a department-specific happy hour to draw in folks in a specific area to your organization and allow them to be recruited in an authentic way.

Avoid Story time with competency-based and / or topgrading interview skills

In order to understand the true history of a candidate’s resume, you should start from dducation and work up. This allows you to ask questions about gaps in employment or other potential red flags in a way that’s chronological and authentic, preventing candidates from being able to hide things or tell drawn-out stories. Topgrading can help you focus on their competencies for the role you are hiring for by seeing how they have evolved from education onward. A good thought to consider — sometimes less experience is more. Especially when hiring for entry-level sales roles, it might be better to take someone fresh out of school so you can mold them and develop them based on your company’s philosophy, not re-train them.

Reduce attrition by focusing on culture and perks

It’s evident that something SalesLoft and Derek Grant and his team have is self-awarness. To retain top-talent, know your audience and know yourself. Focus on experiences and opportunities that will make those you are attempting to retain happy and that are within your means as a department and organization. Grant spoke a lot about offering 80% perks at SalesLoft. An employee might not notice an extra $300 dollars on their paycheck, but they will remember an incentive such as swiming with sharks at the Atlanta Aquariam or free diapers provided by their organization when they become a new parent. Focusing more on memorable perks instead of just traditional bonuses showcases how your organization provides more fulfillment and care than others. As a millennial, I also enjoyed Grant’s take on working with our generation. The idea of “micropromotions” was presented to apease and motivate folks, such as millennials, who may be anxious to get to the next level too quickly. These micropromotions operate as levels within a role (SDR 1, SDR 2, etc…) and there are clear expectations laid out showcasing what you need to do to achieve these promotions and what the outcomes will be. These opportunities are motivating and allow tangible ways for young employees to climb up in the organiztaion.

The Sales Career Journey

At 25, Michelle Baques has just started her fourth role at Sigstr as Director of Sales. Michelle sat down with Sigstr Founder + President, Dan Hanrahan to talk about her journey from Business Development Rep to Director of Sales in less than three years. Dan brought Michelle on as the first member of the sales team in 2015 as a BDR. It quickly became apparent that Michelle was a talent that shouldn’t be wasted, so after two months she moved up to Account Executive. After a year in that role, she made the jump to Senior Account Executive and then just this month was given the opportunity to step into the Director of Sales role.

If you’ve ever had the opportunity to meet Michelle, it’s apparent that she is an extremely driven, hard-working, and motivated person. She is ambitious and works hard to attain her goals. Focusing on goals was a major takeaway of Dan and Michelle’s discussion. Both Michelle and Dan share their goals — personal and professional — with each other frequently, allowing Dan, as a boss, to know what Michelle wants and is hoping to achieve, and for Michelle to understand Dan’s perspective as well. This idea of goal sharing is powerful and I believe helps build a strong culture of trust and understanding on teams. Michelle’s story is also a great example of supporting and rallying behind great talent already existing in your organization.

Operations and Forecasting

Justin Fite, Chief Sales Officer at Lessonly, shared an in-depth look on the alignment of other departments, such as marketing and finance, in the overall operations and executions of the sales team. Overall there is an operational goal of bringing insight and alignment to the sales strategy across the organization. Different departments can serve critical functions for ultimate sales success.

  • Finance and operations can provide top-down guidance and an overview of goals and spend to provide a complete backdrop and direction for the sales team as well as early-warning signs of any upcoming risk.
  • Marketing can assist with the forecast and funneling of leads as well as pre and post sales touch points with enterprise clients
  • AE and SDR managers can be involved with sales strategy.

Fite and his team have worked hard to develop a system where multiple departments can work together effectively to achieve sales goals. Lessons learned in his time as a sales leader on this topic include:

  • Find a cadence that allows for deep-dive by function and re-sync across teams
  • Build great managers in all roles (give empowerment with accountability)
  • Make sure your organization has a strong finance person/team
  • Tie numbers out from top to bottom (channel contribution, expectations, CAC, etc.)
  • Make sure your organization has a strong enablement person/team
  • Have plan, automate knowledge transfer
  • Culture is easy to say…must be authentic and constantly attended to.

Selling to the Enterprise

David Kerr, CEO of Octiv (recently aquired by Conga), sat down with High Alpha Partner, Mike Fitzgerald, for a fireside chat about his experiences selling to the enterprise to close out the day. A great topic that Kerr explored in-depth was focused on selling proof of concepts to large enterprise buyers. The main points Kerr shared to focus on when exploring a POC included:

  • Lock in a full Master Service Agreement
  • Include an out clause
  • Include a fee
  • Define POC success
  • Do a full implementation to increase odds of success
  • Don’t book until after the termination clause has expired

We had a number of other amazing sessions and speakers throughout the day, making for an incredible day of learning, collaboration, and networking across our portfolio companies. 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.