Scaling sales coaching
Coaching was redundant, rigid, and restrictive. I led research and design on a 0-1 feature that contributed to an enterprise customer's renewal.
Company
Ambition
・
Series B
Timeline
6 months
Role
Lead Designer
Team
1 product manager, 1 engineering lead, 2 software engineers





Sales managers are spending more time coaching
Sales managers are spending more time coaching
Sales managers at high-impact organizations are spending 20% of their time coaching.
Sellers want coaching
Forrester data shows that 62% of sellers agree that 'the feedback and coaching I receive helps improve my performance.'
Sales managers need to do more with less
In a challenging economy, we saw managers with upwards of 18 direct reports. Coaching each of them weekly became challenging.
Sales managers at high-impact organizations are spending 20% of their time coaching.
Sellers want coaching
Forrester data shows that 62% of sellers agree that 'the feedback and coaching I receive helps improve my performance.'
Sales managers need to do more with less
In a challenging economy, we saw managers with upwards of 18 direct reports. Coaching each of them weekly became challenging.




Becoming the coaching category leader
Becoming the coaching category leader
Ambition was founded on its gamification features. It later added coaching.
Prioritizing coaching over gamification
As budgets tightened, we noticed trends that customers were churning from gamification. So we shifted our pricing and packaging to highlight our coaching offerings and focused on our new goal: become the leader in sales coaching.
To do that, we needed coaching to be scalable.
How we measured success
Be first to market
Reduce time spent creating coaching by users and CSMs (less manual work)
Increase coaching adoption
Shift market to coaching-first perception
Ambition was founded on its gamification features. It later added coaching.
Prioritizing coaching over gamification
As budgets tightened, we noticed trends that customers were churning from gamification. So we shifted our pricing and packaging to highlight our coaching offerings and focused on our new goal: become the leader in sales coaching.
To do that, we needed coaching to be scalable.
How we measured success
Be first to market
Reduce time spent creating coaching by users and CSMs (less manual work)
Increase coaching adoption
Shift market to coaching-first perception





Following sales mental models
Following sales mental models
Sequences are standard in sales. Studying platforms like this, we found:
Content should be easy to edit
Dragging content was common. Adding content was clear and obvious.
Insights are readily available
These platforms highlighted data related to the content. This seemed especially powerful for monitoring trends and progress over time in order to shape future decisions.
Sequences are standard in sales. Studying platforms like this, we found:
Content should be easy to edit
Dragging content was common. Adding content was clear and obvious.
Insights are readily available
These platforms highlighted data related to the content. This seemed especially powerful for monitoring trends and progress over time in order to shape future decisions.





Sales managers need coaching to be flexible
Sales managers need coaching to be flexible
I conducted 15 interviews with sales managers, sales enablement professionals, and product admins to understand their needs.
Old: redundant, rigid, restrictive
Coaching check-ins had to have the same content. To change agendas, sales managers and enablement professionals had to manually create new events for each person/team over and over. For things like onboarding, promotion paths, and skill development, creating coaching was especially painful for sales enablement.
The problem was so prevalent that our own CSMs were acting on behalf of our customers to set up their coaching.
New: flexible, customizable
The new experience allows sales teams to have custom agendas over time.
I conducted 15 interviews with sales managers, sales enablement professionals, and product admins to understand their needs.
Old: redundant, rigid, restrictive
Coaching check-ins had to have the same content. To change agendas, sales managers and enablement professionals had to manually create new events for each person/team over and over. For things like onboarding, promotion paths, and skill development, creating coaching was especially painful for sales enablement.
The problem was so prevalent that our own CSMs were acting on behalf of our customers to set up their coaching.
New: flexible, customizable
The new experience allows sales teams to have custom agendas over time.





Create coaching content once and add employees anytime
Create coaching content once and add employees anytime
All enablement needs to do now is create the training once then add whoever needs it over time. After launch, we reached out to strategic partners to learn about their experience using it:
Most common use cases
New employee onboarding
Skill development
Career pathing
Most common feature request
Automatically adding employees based on joining a team or performance
All enablement needs to do now is create the training once then add whoever needs it over time. After launch, we reached out to strategic partners to learn about their experience using it:
Most common use cases
New employee onboarding
Skill development
Career pathing
Most common feature request
Automatically adding employees based on joining a team or performance





Easily see employees' progress
Easily see employees' progress
As part of giving visibility, we added tables to show an overview of cadence and employee progress. This allowed them to take relevant actions like: pausing employees, assigning managers, and changing start dates.
As part of giving visibility, we added tables to show an overview of cadence and employee progress. This allowed them to take relevant actions like: pausing employees, assigning managers, and changing start dates.
As part of giving visibility, we added tables to show an overview of cadence and employee progress. This allowed them to take relevant actions like: pausing employees, assigning managers, and changing start dates.

