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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.
(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:
- Offered career growth
- Aligned with her morals
- 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.