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In his Propel22 session, Jerry Henry, Director of Professional Services and Onboarding at Sendoso, talks about the lessons he learned from scaling Sendoso’s customer onboarding team.
Jerry scaled his team from 3 to 15 people in 1.5 years while also reducing the time taken to complete onboarding projects by 35% and significantly improving Sendoso’s CSAT score.
He talked about over-segmentation, forecasting for headcount, data-driven process changes, and how to provide a consistent experience for both onboarders and your customers.
This article provides key insights from the session.
Jerry recommends understanding your company’s scaling goals and then figuring out how the onboarding team can work with that.
During the early stages, CSMs are probably the catchall folks, handling onboarding as a part of their function. However, as you grow, this will not be sustainable. You need different processes. This is when you need to look at processes that can be made repeatable so they are easy to scale. Questions you need to answer:
At Sendoso, they understood that CSMs handling onboarding is not scalable and that they needed to build a dedicated onboarding team. They started with three pioneer onboarders who took the risk to move from CSM into full-time onboarding. Creating an onboarding team helped them crystallize what they needed to focus on: getting customers up and running. The team currently has 15 members.
Next, Jerry moved the onboarding process into a segmentation model. He understood that different categories of customers, such as enterprise and SMB customers had different pain points and needs and therefore needed different onboarding plans and processes. They made sure they segmented their onboarding in three aspects:
Once you understand how the process and tools work, it’s time to become data-driven. Sendoso tracks the following data points:
Having a central data source provides visibility to your executive leaders, your team, and you. Sendoso built an extensive dashboard that shows important metrics such as time to completion, ARR, utilization, number of onboarding projects per team member, CSAT, etc. This helped Jerry and his team use data-backed insights to present requests for hiring, etc., to the executive team.
The next important aspect of scaling a team is hiring. Here is how Jerry looks at hiring:
You need to make individuals feel like they are a part of the team and have a say in how things are done. Here are tips for onboarding leaders to empower team members:
As a leader, if you change a process, but you’re not the one in the trenches, you will probably not understand what is going on. Ensure your team has all the required inputs on any new, significant process. Managers at Sendoso do start-stop-continue meetings every quarter. They evaluate what they aren’t doing but need to start doing, what they need to drop, and what works well and needs to be continued.
As the leader, you may not be working with the team members side-by-side every day. Ensure that the rest of the team has a say in who you hire.
Pick leaders from within the team. Sendoso helps team members understand what they need to do to grow their careers at Sendoso; Sendoso has also invested in learning platforms to help team members upskill. Even if not within Sendoso, they set their team members up for success as an onboarding professional
Empower your team members to take on strategic projects such as process changes. Sendoso includes the team leads and managers from their onboarding function in cross-functional meetings to gain visibility and provide the onboarding point of view for decisions.
Here are quick takeaways from the session:
“Speeds up CSV importing and saves me from having to get customers to use a template file or create mapped data exports. Quick to integrate and flexible outside the happy path. We found defining workbooks and templates confusing; at a prior job it was configured through code, which I preferred.”
Source: G2 review


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A Forward Deployed Engineer (FDE) embeds in the customer environment to implement, customize, and operationalize complex products. They unblock integrations, fix data issues, adapt workflows, and bridge engineering gaps — accelerating onboarding, adoption, and customer value far beyond traditional post-sales roles.





70–85% utilization. 94% G2 rating.
One platform does what the entire table above tries
to split across tools.
70–85% utilization. 94% G2 rating.
One platform does what the entire table above tries
to split across tools.

70–85% utilization. 94% G2 rating.
One platform does what the entire table above tries
to split across tools.
Enterprise implementations fail because customers don’t follow the process or provide clean data on time. Most delays are purely “customer-side” issues.
Implementations fail because complex environments need real-time technical problem-solving. FDEs unblock workflows, integrations, and unknown constraints that traditional onboarding teams can’t resolve on their own.
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Companies that embed engineers directly with customers see significantly higher enterprise retention compared to traditional post-sales models — because embedded engineers uncover “unknowns” that never surface in ticket queues.

VP Sales, Intercom

A Forward Deployed Engineer (FDE) embeds in the customer environment to implement, customize, and operationalize complex products. They unblock integrations, fix data issues, adapt workflows, and bridge engineering gaps — accelerating onboarding, adoption, and customer value far beyond traditional post-sales roles.






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