Episode OneHundredEightyNine

The Transition From Player to Coach

Guest: Kaitlen Kelly, Sales Development Team Lead – EMEA at Outreach

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About This Episode

You used to be able to plan your week on, say, Sunday night.

Now you have your calendar open constantly for next month.

I had a chance to chat with Kaitlen Kelly, Sales Development Team Lead – EMEA at Outreach, about being a new SDR team lead.

(Actually, the day we recorded was Kaitlen’s one-year anniversary at Outreach! Congratulations!)

“In December I took the leap from player and started leading the UK team out of London,” Kaitlen said. “Super excited to announce we’ve taken that team from 3 SDRs to 10 SDRs, and in Q1 as the official coach of the team over there, we were able to achieve 173% of plan to quota.”

So, obviously, she’s killing it.

Let’s dive into her insights and learnings from her first 6 months in the coach’s spot!

Successful career transitioning

Kaitlen was in the fashion and merchandising sales industry for 6 years before transitioning to tech sales. 

“Being in that environment where it was self-motivated and goal-driven, you had your team around you to support and achieve,” Kaitlen said. “I always knew I wanted to stick with that spark.”

She broke into the SaaS industry through a mutual connection and looked for these qualities in a company:

  1. Offered career growth
  2. Aligned with her morals
  3. Provided meaningful opportunities

She was a successful individual contributor from the start, but thinking about what she really wanted her impact to be was what interested Kaitlen in leadership.

“I would rather build somebody up and win as a team than have me be the one standing on the podium alone,” she said.

That team mentality has helped her commit to coaching brand new SDRs — probably their first jobs out of college.

“It was important for me to make sure that they came into this company and felt supported, had the right people around them, and felt like they could achieve their goals,” she said.

In terms of having a meaningful, teamwide impact, Kaitlen is inspired by the opportunity to coach young reps and watch them improve over time.

The unexpected in leadership

All the scheduling

Kaitlen shared that even as a type A person who loves to plan, she has had to up her scheduling game.

As an individual contributor, she had only her own agenda to organize.

Now she’s responsible for a team of 10.

“As you’re navigating so many different things on your plate, I’m building out my plans 100% in calendar at least two to three weeks out for my team,” she said.

Training for the basics

The UK team is such a new market that Kaitlen is facing a steep learning curve for building out sequences.

She onboarded 3 reps with no sales experience.

“You’re teaching them the basics of cold calling and how the platform works… and then you’re adding 2 more on… and then you’re adding 4 more on,” she said.

Paying attention to structure and process really helped Kaitlen catch gaps in their training and in her own leadership development.

2 critical sales leadership tips

A lot of team leads were SDRs last week — first a peer, now a manager.

1. Know your team

“The biggest thing to make that a smoother transition is leverage the reps,” Kaitlen said. “Play up their strengths.”

When you were a peer, you were still a resource to the other players. Now that aspect of your position has expanded.

As a manager, if you can be seen as a resource to help your team develop, you’ll be able to identify and lean on them for their strengths even more.

2. Grow your team

Kaitlen’s leadership style places high importance on people and their wellbeing.

  • Develop reps holistically. Don’t just track outcomes, track habits that develop behavioral competencies.
  • Be human. People don’t work for “companies” — they work for people. Get to know your people, and let them know you.

Kaitlen prioritizes weekly one-on-ones that are led mostly by the rep as far as what they dig into.

She also shares her vulnerabilities with her reps.

On her first day at Outreach, Kaitlen was put on the spot to report on how her first meeting went. Alright, I’ve just got to jump into this. Now’s the time, she thought.

“I’ve carried that mindset throughout my entire journey with Outreach. I would just get comfortable with the uncomfortable, basically,” she said.

Get in touch with Kaitlen on her LinkedIn and especially at SDRs Anonymous.

For more engaging sales conversations, subscribe to The Sales Engagement Podcast on Apple Podcasts, on Spotify, or on our website.

About The Podcast

The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real-life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.

Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.

The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.

Hosted by Joe Vignolo, Senior Content Managing Editor at Outreach, and Mark Kosoglow, Vice President of Sales at Outreach.

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