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Draft Your B2B Customer Success Roster

by Allyson White

Insight Onsite hosted a "Let’s Discuss” forum for our CS community on hiring CSMs and designing an organization for scale.  Some of the learnings and perspectives are summarized below. 

Ask a Customer Success leader what is top of mind and hiring invariably makes the top three. 

Customer Success leaders in Insight’s portfolio invest much of their time and energy into hiring, recruiting and building their team.  In 2018, our growth stage companies had, on average, three open customer success positions per quarter. As your business and customer base scales, the customer success team and processes that will drive productivity must scale as well. 

Competition, especially for mid-career and experienced CSMs, is fierce.  Across the industry CSM positions increased more than 90%2, and as result voluntary attrition has ticked up often to 3 – 5% per quarter.

Tips from the Community: Hiring and constructing a CSM team?


1) Stop looking for "purple squirrels" or "ninjas"

Frequently teams initially search for the CSMs who can “do it all”; they are technical, build strong relationships, know how to navigate large organization, and are masters at the tough conversation around renewals and tough negotiators. Early hires often are generalists who can juggle multiple roles and already know your industry.  Often these individuals are former clients, have worked for a competitor or have worked for a company that also sold to your customers, and have sales or negotiations experience. 

At the growth stage, our advice is to stop looking for the “purple squirrels" or “ninjas.”  There are few of these people out there. As a result, this hiring strategy won’t scale.

2) Uncover opportunities for specialization

Portfolio leaders recommend breaking out the critical contributions of customer success in your organization, particularly around relationship building, product expertise and project management, and drafting a team of specialists.  

The profiles needed relate to two factors, namely product complexity and contract size. Leaders recommended keeping three questions in mind as you think about each customer segment: 

  • How technical is your product? 
  • How large are your contracts?
  • What types of relationships do you need to drive value and expand this customer account? 

In technical products with large contracts, teams shared variations of pod structures, which included a relationship lead, a technical expert (often called a solutions architect or consultant) for product expertise, and onboarding specialists and, at times, dedicated trainers.  

In smaller contracts with less technical products, teams have hired more data-driven teammates often adept at building, testing and iterating programmatic customer outreaches. For example, launching an email outreach campaign when a feature is underutilized 3 months after onboarding. Some even have marketing and B2C backgrounds rather than B2B experience. These teams also include dedicated teammates to manage and collaborate with marketing and product on self-service materials.

3) Consider content and self-service documentation as member of the team

When self-service documents and reporting tools are in place, leaders can invest in up-leveling the team’s skillset. They can trade a few junior team member hires – needed for reporting basics, routing simple customer questions – and add a more experience team member to focus on proactive customer engagement.

Support tickets and interviewing your existing team will help write the “job description” for self-service materials (in other words, what types of content and collateral to build). Most teams have found that at baseline between 30% – 40% of inbound request could be solved or resolved faster when customer success teams had access to knowledge center content and documentation. 

As a bonus, documentation also helps ease employee onboarding for scaling companies constantly adding to the customer success department. Customer-facing materials could be tweaked for employee onboarding and improved consistency in onboarding experience. 

4) Always be on the lookout for talent 

Finally, CS community leaders suggest having a continual shortlist of the people you will call when – not if – there is an opening on your team.  Openings are inevitable, so plan ahead. People on your shortlist may not be available, but they often can refer a colleague to jumpstart your pipeline. 

Let's us know your thoughts! What ways you are stretching your customer success organization? What roles and profiles are you investing in to scale your customer success organization? Please email ivpmarketing@insightpartners.com

1 Insight internal data. 
2 LinkedIn research.

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Allyson White

Principal, Onsite

Allyson joined Insight in 2012. Previously, she was a strategy consultant in the markets and customers practice at Monitor Group, where she advised multi-national companies on growth strategy, product innovation, acquisitions, scenario planning and pricing strategy.¬†She worked in a variety of…

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