How Checker’s transitioned from inbound to outbound sales
(And scaled their sales team from 14 to 150 reps)
Read time: 3 min
Last week, I listened to this episode on How to Build a Billion Dollar Outbound Sales Team w/ Carrie Bosworth (SVP Sales, Checkr), on the Science of Scaling podcast from Mark Roberge.
Carrie talked about scaling a sales team from 14 to 150 reps and changing from inbound to outbound sales.
I have been part of a company going through a similar transition.
This change is hard, but possible.
Here are my 12 lessons from the episode
1) Scaling with Inbound Leads Only
Rarely do companies hit massive revenue through inbound alone.
When Carrie joined Checkr, they were scaling fast but knew inbound would eventually slow down.
They started outbound to keep up their growth.
2) Transition Challenges
Moving from inbound to outbound is hard.
Different rep profiles and skill sets are needed.
How you hire, create materials, and approach the market changes.
3) Outbound takes time
It took Checkr 6-9 months to get ready for outbound.
4) Executive Involvement
Executives should think, AND also engage in outbound.
Everyone is involved in outbound: individual contributors, leaders, and executives.
Reps write notes for execs, who adjust them to sound authentic.
Execs don't run long sequences.
Execs don’t run long sales sequences
They are asked to reach out to top accounts because their involvement increases the chances of success. They also ask their CPO, CTO, CEO, and board members to contact peers at target accounts.
5) Deep Research for Enterprise AEs
Mark Roberge shared how Enterprise AEs work:
AEs with public company accounts spend 2 months on research before reaching out.
They buy the prospect’s product, use the app, create detailed reports, print them, and send them to marketing executives.
This deep research helps them book meetings and close deals faster.
6) Inbound to Outbound Transition
Initial AEs were order takers and had no experience as BDRs (Outbound).
Given a chance to switch, then many opted out or moved to other teams.
Most the AEs didn't have the skill sets needed for this transition.
7) Hiring and Expectations
For leaders, AEs, BDRs, and SDRs:
Leaders: Need outbound experience, not just their team members. They should have led teams of AEs doing outbound sales.
AEs:
Need outbound experience. Note: having BDRs book meetings for you does not count as outbound experience.
Enterprise AEs need more experience, and tenure.
Their pipeline should be:
50% from outbound/BDR
50% from Marketing/Partner
Reps should not rely only on marketing for leads; they need to take responsibility. If they don’t meet their quota, they shouldn’t blame marketing.
Note: When Checkr launched outbound sales, they didn’t have a BDR team, but they still required AEs with outbound experience.
BDRs (Outbound)
They require 1 year of BDR experience at top companies with strong training programs like Salesforce, ADP, and HubSpot.
SDRs (Inbound)
They are often recruited from college athletes for their motivation and work ethic.
8) Territory Management
Started with 14 reps using a Round Robin system.
As they grew to 150 reps, they balanced territories based on company size and ICP.
9) ICP Definition
They focused on Lifetime Value (LTV), retention, and Customer Acquisition Cost (CAC).
High LTV accounts don’t always have the lowest CAC.
If they only focused on win rate or inbound flow, they would have a business with high churn.
10) Territory Alignment Post-Covid
They shifted from geographic focus to ICP focus after COVID.
The best ICPs guided segmentation.
They focused on fairness for the team, looking only at size and industry, not geography, because communication was mostly via video or call.
They created extra territories to prepare for growth:
They planned 20% more territories to ensure they had enough accounts when they hired more reps.
When they planned the year, they temporarily gave extra territories to existing reps, but these would be reassigned to new reps as they joined.
11) Switch from an Inbound to Outbound Playbook
Inbound playbook: reactive, focused on product knowledge, moving quickly through the sales cycle, ensuring AEs have coverage, and working with marketing.
Outbound playbook: require operational discipline: Every day matters.
Dedicated time for outbound activities is crucial:
What do you do from Monday to Friday to make progress?
Balance outbound activities with current opportunities
Ensure both reps and leaders dedicate time to outbound. If you don’t, it won’t get done.
12) Accountability Measures
Monthly scorecards with more weight on outbound activities.
Daily dashboards to track progress
Hold pipeline meetings at the start of the week and forecast meetings at the end of the week.
Outbound sales require strategy, preparation, and the right team.
P.S. What do you find most challenging when shifting from inbound to outbound sales?
Now you have some ideas on what you need to work on if you want to transition your inbound sales team to outbound.
That’s it!
I hope this helps you on your Outbound journey.
✌️👨🍳
Elric
P.S. I’m sending you this newsletter from the Alps after a week in sunny Nice, France. 🇫🇷 The new branding is almost ready, and our designer has sent us the new logo. I can’t wait to share it with you when it’s ready.
As soon as you're ready, I can help you in 3 different ways:
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