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Scaling up your sales
managers:
5 mistakes new leaders make
Jane Kim
Chief Revenue Officer,
CircleCI
← first-time
manager here
● Hired 150+ people at SuccessFactors, SAP, Optimizely, now
CircleCI
● Scaled global teams
● Generated $200M+ of annual revenue growth
● Promoted and developed 20+ first time managers
Learned a lot in the 10+ years as a leader.
But, your people have to scale too
SaaS = software that scales.
5 mistakes new leaders make.
You can’t avoid them.
Don’t try.
Instead, build resilience.
● Recognize the problem in order to recover quickly
● Learn from your mistakes
● Build trust as a team
Why is resilience so important?
● As a leader, you say a lot more NO than YES
● Being a leader is lonely
● As you grow your team, the stakes get higher
● Making decisions is hard. You WILL make mistakes
● Resilience will allow you to keep growing
Mistake 1:
You will micromanage
Micromanagement is the fastest way
to disempower and demotivate a
team.
Get to know your team to build trust.
TO RECOVER:
● Everyone has their own unique set of strengths,
weaknesses, and experiences
● Help each individual find their best way to success
● Get them to that light bulb moment when they make it
their own
Mistake 2:
You will hire the wrong person
Hiring at scale, you will hire the wrong person.
● It’s not about the individual, it’s about fit
● Keeping someone in the wrong role is a disservice to you, the
company, and most importantly, to them
Focus on the overall health of the team.
● Trust the process. It’s not just about 1 or 2 hires
● Focus on training and development for your whole
team
● Know performance levels so you know how to invest
TO RECOVER:
Mistake 3:
You will want your
team to like you
Your ultimate goal is building a successful team.
● Hard to transition from a peer to a boss
● As a leader, it’s not your job to be liked
● Sometimes that means making the tough call
Take your ego out of your vision of success.
● It’s not about you. It’s about them
● Trust you’re making decisions for the right reasons
● Build a resilient organization that can thrive
● Everyone wants to be on a high-performing team with a
leader they trust to get them there
TO RECOVER:
Mistake 4:
You will give bad advice
When your team says, “What do I do?” and
you don’t know the answer, you have 2 options:
● Jump to conclusions
● Admit you don’t have all the answers
Your team can smell BS a million miles away.
← what I did
Pause, learn more, reflect.
● Taking time to understand a problem can feel vulnerable
● Ask yourself: do you really understand the root cause
problem?
● Listen + learn before you jump to solutions
TO RECOVER:
Mistake 5:
You will pursue the
wrong strategy
As a leader, you may set the wrong strategy.
● Stakes only get higher as you grow
● Hindsight is always 20/20. Foresight makes you as blind as a
potato
You have to be resilient.
TO RECOVER:
● You can only make the best decision with the
information you have at the time
● Build trust in yourself, your team, and your judgment
● Learning from your mistakes means you will head in
the right direction, no matter what
Micromanagement
Hire wrong person
Likability trap
Give bad advice
Pursue the wrong strategy
Doubt yourself
Resilience allows you to face any challenge.
● Be focused on where you’re trying to go
● Experiment and learn from your mistakes
● Put your team first
● 7 people
● 1 office
● Unproven sales process
2.5 years ago:
● 50+ people and 200+ employees
● 4x Revenue growth
● San Francisco, Boston, Denver, Tokyo, now Europe
● Platform at 25M builds per month, 30k+ customers
We’re hiring!
today:
My core job is to make decisions.
Sometimes I have decision fatigue, but not decision
paralysis.
Honing your ability to be resilient is critical to your success
as a leader, and as a company.
Thank you

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Scaling Up Your Sales Managers: 5 Mistakes New Leaders Make with CircleCI

  • 1. Scaling up your sales managers: 5 mistakes new leaders make Jane Kim Chief Revenue Officer, CircleCI
  • 3.
  • 4. ● Hired 150+ people at SuccessFactors, SAP, Optimizely, now CircleCI ● Scaled global teams ● Generated $200M+ of annual revenue growth ● Promoted and developed 20+ first time managers Learned a lot in the 10+ years as a leader.
  • 5. But, your people have to scale too SaaS = software that scales.
  • 6. 5 mistakes new leaders make. You can’t avoid them. Don’t try.
  • 7. Instead, build resilience. ● Recognize the problem in order to recover quickly ● Learn from your mistakes ● Build trust as a team
  • 8. Why is resilience so important? ● As a leader, you say a lot more NO than YES ● Being a leader is lonely ● As you grow your team, the stakes get higher ● Making decisions is hard. You WILL make mistakes ● Resilience will allow you to keep growing
  • 9. Mistake 1: You will micromanage
  • 10.
  • 11. Micromanagement is the fastest way to disempower and demotivate a team.
  • 12. Get to know your team to build trust. TO RECOVER: ● Everyone has their own unique set of strengths, weaknesses, and experiences ● Help each individual find their best way to success ● Get them to that light bulb moment when they make it their own
  • 13. Mistake 2: You will hire the wrong person
  • 14.
  • 15. Hiring at scale, you will hire the wrong person. ● It’s not about the individual, it’s about fit ● Keeping someone in the wrong role is a disservice to you, the company, and most importantly, to them
  • 16. Focus on the overall health of the team. ● Trust the process. It’s not just about 1 or 2 hires ● Focus on training and development for your whole team ● Know performance levels so you know how to invest TO RECOVER:
  • 17. Mistake 3: You will want your team to like you
  • 18.
  • 19. Your ultimate goal is building a successful team. ● Hard to transition from a peer to a boss ● As a leader, it’s not your job to be liked ● Sometimes that means making the tough call
  • 20. Take your ego out of your vision of success. ● It’s not about you. It’s about them ● Trust you’re making decisions for the right reasons ● Build a resilient organization that can thrive ● Everyone wants to be on a high-performing team with a leader they trust to get them there TO RECOVER:
  • 21. Mistake 4: You will give bad advice
  • 22.
  • 23. When your team says, “What do I do?” and you don’t know the answer, you have 2 options: ● Jump to conclusions ● Admit you don’t have all the answers Your team can smell BS a million miles away. ← what I did
  • 24. Pause, learn more, reflect. ● Taking time to understand a problem can feel vulnerable ● Ask yourself: do you really understand the root cause problem? ● Listen + learn before you jump to solutions TO RECOVER:
  • 25. Mistake 5: You will pursue the wrong strategy
  • 26.
  • 27. As a leader, you may set the wrong strategy. ● Stakes only get higher as you grow ● Hindsight is always 20/20. Foresight makes you as blind as a potato
  • 28. You have to be resilient. TO RECOVER: ● You can only make the best decision with the information you have at the time ● Build trust in yourself, your team, and your judgment ● Learning from your mistakes means you will head in the right direction, no matter what
  • 29. Micromanagement Hire wrong person Likability trap Give bad advice Pursue the wrong strategy Doubt yourself
  • 30. Resilience allows you to face any challenge. ● Be focused on where you’re trying to go ● Experiment and learn from your mistakes ● Put your team first
  • 31. ● 7 people ● 1 office ● Unproven sales process 2.5 years ago:
  • 32. ● 50+ people and 200+ employees ● 4x Revenue growth ● San Francisco, Boston, Denver, Tokyo, now Europe ● Platform at 25M builds per month, 30k+ customers We’re hiring! today:
  • 33.
  • 34. My core job is to make decisions. Sometimes I have decision fatigue, but not decision paralysis. Honing your ability to be resilient is critical to your success as a leader, and as a company.