Leadership Lab

Part 5: Enablement

In this environment, everything changes, fast. Enablement needs to occur at every level on a frequent cadence.

LinkedIn Logo
Maya Connet: VP of Inside Sales at Clari

Show what great looks like

Getting reps bought in and trained means showing them what works, starting with your CEO, CRO, VPs, and top performing reps doing the outbound work.

Creating easy ways for the team to share and celebrate the wins (both large and small). Most leaders we've talked to have created a slack channel where ICs can share the emails, linked-in messages, cold call scripts, personalized touches, etc. that landed the meeting, or got them the right referral.

maya connet
Maya Connet
VP of Inside Sales

"The number one thing that we've done is that we are constantly highlighting the successes of the folks who are doing it well. So we do more peer-to-peer enablement than we do any other type of enablement across the board."

Manager enablement

It starts at the top.The biggest enablement miss is focusing solely on reps and not on managers. Your first and second line managers are the enforcers, the enablers, the educators, and the motivators. Just because someone was a good IC seller does not mean they know how to teach the tactics that made them successful.

Time spent training managers on how to integrate the strategy and playbooks, interpret numbers to provide guidance, and to bring rigor to their teams will trickle down across the entire sales force. Rep training often gets stuck at a few reps.

Make sure your managers are prepared with tools and skills like:

  • 1-1 templates to ensure they are talking about PG every week
  • Dashboards with the right visibility into leading indicators so they can coach properly
  • The ability to interpret data and double click on the root of the problem

How to have a good 1:1

Accountability starts with the 1:1. Make sure you're not spending 100% of your time on deal gossip and each others weekends.

In reality, great management is the blending of the metrics and the strategy in order to go two and three levels deeper with reps and drive results. Make sure managers know how to balance accountability into metrics and how to double click to find the root of low performance.

Managers are the first line of implementing the right culture. They are the ones who should be asking: Are reps on their team aware of how inconsistent they are? Are they simply not working enough accounts? Are they unable to convey value succinctly? Can we teach them to self-diagnose what needs to be adjusted?


Although the frequency of enablement sessions across these teams was varied, all teams had enablement at least twice a month.  Why? Because in this market what is working changes quickly.

Steve Travigelli grew Linksquares from $0-50MM with 90% coming from outbound. When he introduced outbound, they went from v1 of their messaging/cold call scripts to v12 in just 3 months. That’s an update a week based on real time feedback. 

Don’t let perfection be the enemy of good. Steve rolled out micro-enablements to focus on one small topic at a time like cold call openers, or top objections rather than build out a long formal training. Clari has a weekly meeting where they roll out new experiments or plays for teams to leverage. At Snapdocs, Brian Michaels had a team meeting to share out tactics that were working every other week.

Enablement topics

There is never a shortage of what you can be enabling your team on. As Daisy Chung said, "Everything is constantly changing."

Steve Travaglini
Steve Traveglini
CEO, former CRO

"We'd focus on cold call openers or cold email openers...We'd teach them how to develop that skill of being able to write custom copy from scratch that has taste and style, which I still think has an edge over some of the AI stuff today... We would hand the reigns to a different person each time so it's not just the same broken record, same person every single time."

The top topics that are must haves on your enablement calendar include

  • ICP enablement: training on qualified accounts and people
  • Developing an account plan complete with creating a unique point of view, performing research, and finding the right people
  • Effective messaging per channel with topics like: how to email execs, cold call openers, linkedin messaging (vs. email)
  • Ramping on a specific cross functional campaign or playbook in partnership with marketing
  • How to timeblock for effective time management

Live Session: How to Account Plan

Contentsquares' RVP of Enterprise Sales, Shea Brucker, joins Todd Busler for a session on how to use an Account Plan to break into Enterprise Accounts.


Want more?

Get exclusive leadership advice, tactics, and interview content here.

Thank you! You have been subscribed!
Oops! Something went wrong while submitting the form.