Unlocking sales potential through scalable 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.
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
Timeline
Role
Team
Ambition
6 months
6 months
Lead Designer
1 PM, 1 Engineering Manager, 2 Software Engineers
Company
Timeline
Role
Team
Ambition
6 months
6 months
Lead Designer
1 PM, 1 Engineering Manager, 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 to be coached
Forrester data shows that 62% of sellers agree that 'the feedback and coaching I receive helps improve my performance.'
Sales managers are being asked 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 to be coached
Forrester data shows that 62% of sellers agree that 'the feedback and coaching I receive helps improve my performance.'
Sales managers are being asked 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.




Positioning company as the category leader
Ambition was founded on its gamification features. It later added coaching.
Becoming coaching-first
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.
Becoming coaching-first
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
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 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 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 needed flexible, scalable coaching
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 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
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.
Early-adopters and platform saw growth
Sellers can now get more coaching easily.
As one customer put it:
"…It’s not in that manager’s capacity to track each reps’ 30/60/90. Ambition Coaching Cadences will remove that manual work."
Similarly, a CSM reported this from an enterprise customer:
"…they found those who completed 80%+ of their cadence check-ins were performing better than their peers among many of the KPIs for new hires."
New content and roles
We saw LMS content added which spurred on an integration with Lessonly. Additionally, new roles like internal training members, HR members, and enablement professionals started using the platform.
Sellers can now get more coaching easily.
As one customer put it:
"…It’s not in that manager’s capacity to track each reps’ 30/60/90. Ambition Coaching Cadences will remove that manual work."
Similarly, a CSM reported this from an enterprise customer:
"…they found those who completed 80%+ of their cadence check-ins were performing better than their peers among many of the KPIs for new hires."
New content and roles
We saw LMS content added which spurred on an integration with Lessonly. Additionally, new roles like internal training members, HR members, and enablement professionals started using the platform.
Becoming enterprise-ready
In many ways, we succeeded:
First to market
Reduced amount of time creating coaching (anecdotally from customers and CSMs less involved)
Grew the platform
Yet in others, we missed the mark:
Created confusion by not having parity amongst similar features
Lacked high adoption
Overall, the project was a success. While I don't think we had enough enterprise customers with dedicated sales enablement teams to truly see the value, the feature was used to sell to them.
View another project
In many ways, we succeeded:
First to market
Reduced amount of time creating coaching (anecdotally from customers and CSMs less involved)
Grew the platform
Yet in others, we missed the mark:
Created confusion by not having parity amongst similar features
Lacked high adoption
Overall, the project was a success. While I don't think we had enough enterprise customers with dedicated sales enablement teams to truly see the value, the feature was used to sell to them.