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.

View another project