About this role.
This senior customer onboarding leader manages a team of onboarding managers for a vertical SaaS/ERP platform serving community associations. The role owns the end-to-end onboarding and enablement program, with accountability for software adoption, digital-payment utilization, delivery quality, and customer outcomes. It combines people leadership, program redesign, operational metrics, escalation management, and cross-functional work with Sales, Product, and Customer Success. The manager will guide implementation activities including data migration, setup, activation, and workflow change management. The position is a US-remote build role requiring EST availability and approximately 10% travel.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
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Sample interview questions
I began by mapping the existing customer journey, team capacity, delivery bottlenecks, and adoption outcomes. I then introduced defined milestones, ownership rules, standardized playbooks, and a weekly metrics review, which made risks visible earlier and improved consistency. I would use the same diagnostic-to-execution approach at Enumerate, with particular attention to payment adoption and time-to-value.
I establish a small set of outcome measures, such as on-time go-lives, activation completion, product utilization, customer satisfaction, and quality-review results. In regular one-on-ones, I use call reviews, account plans, and performance data to identify one or two specific coaching priorities, then follow up against observable behaviors and results. Clear expectations, direct feedback, and repeatable coaching cadences help turn strong individual practices into a consistent team standard.
I would segment customers by readiness and workflow complexity, then connect payment adoption to practical outcomes such as reduced manual work, better visibility, and more reliable processing. The onboarding journey should include role-specific enablement, clear activation milestones, proactive risk flags, and follow-up usage data after go-live. I would also equip the team with objection-handling guidance and escalate product or process friction that repeatedly blocks adoption.
I first clarify the customer impact, data-integrity risk, launch timeline, and accountable owners. I create a concise recovery plan with decision points, communication cadence, validation steps, and criteria for proceeding or delaying activation. Internally, I bring the right product, technical, and customer-facing partners together while maintaining one clear customer narrative and documenting preventative actions for the onboarding playbook.
I would prioritize high-volume, repeatable work that slows onboarding managers without improving the customer relationship, such as meeting summaries, implementation-plan drafts, readiness checklists, risk scoring, knowledge retrieval, and follow-up creation. Each workflow would be piloted with quality controls and measured against time saved, milestone completion, adoption, and customer satisfaction. Automation should give managers more capacity for change management and strategic customer coaching rather than simply adding tools.
Enumerate is looking for a Senior Manager of Customer Onboarding to join our team!
The Senior Manager of Customer Onboarding is a quality, performance, and execution leader accountable for the output of a team of onboarding managers. You will build and run the program that drives software adoption, customer competence with new digital workflows, and — above all — payments utilization. The ideal candidate is a proven people leader who knows how to get high performance out of individual contributors, holds the team accountable to the playbook, and has a track record of enabling customers for continued revenue growth while coaching others to do the same.
Responsibilities:
- Build and lead a high-performing team of onboarding managers — set clear expectations, coach to the top of each person’s range, and develop them into consistent performers.
- Own the end-to-end onboarding experience — smooth transitions, on-time delivery, and the quality standard of a best-in-class program for this industry.
- Own the strategy that drives customer enablement and payments adoption, ensuring key utilization metrics are met and customers are positioned for continued revenue growth.
- Act as an escalation point for complex onboarding challenges, collaborating with other teams to resolve issues.
- Guide the team and customers through data migration, setup, and account activation, ensuring data integrity and security
- Redesign how onboarding gets done — you’ll have real latitude to experiment with AI and tech-enabled workflows that cut time-to-value and lift customer satisfaction
- Own the enablement program end to end — playbooks, milestones, and coaching cadences that produce measurable software adoption, workflow competence, and payments utilization, benchmarked against the best in the industry.
- Run a tight performance rhythm — 1-on-1s, team reviews, and metrics that tell you where to coach next — addressing gaps early and directly.
- Partner with Sales, Product, and Customer Success to align efforts and deliver a seamless client experience, and report on onboarding metrics, team performance, and program improvements to leadership.
Requirements:
- 6-10 years of experience in SaaS onboarding, implementation, or similar roles, with at least 3 years leading a team of individual contributors. This is not a first-time management role — you must have already owned team performance, including coaching, accountability, and managing underperformance to a standard.
- Demonstrated success driving software adoption and payments or digital-workflow utilization, with metrics you can speak to.
- Proven ability to coach others to the same results — developing individual contributors into consistent, high performers.
- Experience designing or rebuilding an onboarding or enablement program — playbooks, milestones, quality standards — not just running one someone else built, with the project management discipline to hold competing priorities together. Experience applying AI or automation to service delivery is a plus.
- Excellent communication and relationship-building skills, with the confidence to guide accounting and operations stakeholders through changes to their own workflows — including the shift to digital payments. Data migration should be familiar territory as part of initial setup and activation; you don’t need to have run large migrations yourself, but it can’t be a foreign concept.
- One of two backgrounds, and we want to see both: (a) hands-on understanding of association management and fund accounting — you know what a solid, efficient accounting setup looks like and what these customers need to be successful; or (b) a strong track record leading onboarding or implementation teams in vertical SaaS or ERP, with the appetite to go deep on fund accounting fast. Candidates who bring both will move quickest, but the deciding factor is whether you want this role specifically — tell us why.
- Bachelor’s degree preferred but not required.
Why Enumerate:
We’re a fast-moving, high-growth company building the association management ERP platform that community associations and the companies who manage them run on — a vertical SaaS market that is only now going digital. Which means the playbook for onboarding, enablement, and payments adoption is still being written, and you’d be the one writing it. There is a deep backlog of AI and tech-enabled operating workflows waiting to be built, and the appetite to try them. If you like owning a number, redesigning how the work gets done, and seeing your changes land in weeks rather than quarters, this is a fun place to be. This is a build role, not a caretaking role — you’ll shape the program, the team, and the standard the industry gets measured against. When you apply, tell us why you want this job specifically. We’re far more interested in that than in a perfectly matched resume.
This is a remote role, but candidates must be located in the United States and able to work EST hours. 10% travel requirement is anticipated.
The pay range is inclusive of base salary plus any applicable bonuses or commissions.
Total compensation pay range (annual salary):
$100,000—$120,000 USD
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