GTM 19: The Art of Sales Leadership

GTM 19: The Art of Sales Leadership

Sales are an essential component of any successful companies. As such, it is important for companies to invest in developing strong leaders who can lead their sales team to success. 

In this episode, we are joined by Rick Smolen. Rick is the current Head of Sales at Loopio. He is a results-focused revenue leader with over 20 years of experience in tech and enterprise software sales. 

Rick used to be the Head of Sales at Greenhouse Software, where he oversaw the company’s annual recurring revenue tripling to over $65 million in less than three years. Prior to that, he spent over a decade at Interlinks in sales, sales leadership, and international roles, and helped the company grow to over $300 million in annual sales.

In this episode, you will learn:

  1. How to transition from a great salesperson to an effective people leader
  2. Three sales methodologies, when to use them, and how to teach them
  3. How to sell in a different global market 

Highlights

(1:25) Rick’s background

(4:13) Rick’s first management role and career journey

(8:08) His opinion on promoting your top sales rep to leadership

(11:00) How to foster people management skills 

(11:20) The value of mentorship in developing leadership skills

(14:20) Why transparency is key in team and leadership building

(16:40) How to deliver/receive tough feedback constructively

(18:18) Three different sales methodologies, when to use them, and how to teach them

(25:40) Rick’s learnings from spending 12½ years at a company

(29:40) Rick’s experience and learnings from selling in Asia

(33:52) Comparing doing business in North America and Asia

(37:37) Strategies to keep your team motivated through tough times in 2023

(41:28) One actionable strategy Rick has used to increase revenue

Quotes

The reason I got into management wasn’t because I was some great people leader; it was because I was great at sales.

When you have people on your team that can help you recognize blind spots when they happen, it’s a prerequisite so that you can make sure things don’t go off the rails.

If you’re an effective leader, you have more than one person on your team that has enough vulnerability-based trust that we can just get past all the BS and just be real with each other. I don’t think a leader needs to have an entire team with that one-to-one type of relationship, but it’s probably good to have one or more of those relationships on the team.

If you think about a career in sales, your first year in a role is really trying to get your feet under you. The second year, maybe you start to kind of thrive. By year three, you’re like an expert in that company.

If you’re going to go into a new geography, don’t dip your toe in. You got to either go big or serve it from some other place.

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Before helping found GTMfund, Scott spent 4 years at Outreach as Director of Strategic Engagement. He was in charge of aligning key relationships with VCs, BoDs, ecosystem partners and community members to drive revenue and strategic initiatives across Outreach. Scott initially ran revenue/partnerships for Sales Hacker (which was acquired by Outreach in 2018). Prior to Sales Hacker, he led and built outbound Business Development teams at Payfirma and MediaValet. Scott also advises for a number of high growth start-ups and is the host/author of The GTM Podcast and The GTM Newsletter. At GTMfund, Scott leads all fundraising efforts and runs the media arm of the firm. He’s also responsible for assessing investments, team management, LP/community relationships and GTM support for founders.

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