Full time • On-Site

Plum Benefits, LLC; Eastern Ontario; On-site; CAD 110,000 - 170,000; Full time

Job summary

Plum is seeking a senior onboarding leader to drive activation for our largest customers. You will own the onboarding journey from pre-sales through closeout, coordinating with account managers and insurers to ensure a seamless handoff and value realization.

With 7–8 years total experience and strong stakeholder management, you will guide training and consult on product best practices, using AI to elevate the customer activation experience.

Qualifications

• Experience leading onboarding teams for enterprise customers.
• Ability to align cross-functional stakeholders to drive activation.
• Interest in AI and using data to improve customer journeys.

Responsibilities

• Lead onboarding for top customers from pre-sale to closeout.
• Partner with Account Managers and Insurers to ensure smooth handoffs.
• Define timelines and drive activation milestones in 30-day window.
• Report metrics and customer feedback to spot improvement opportunities.
• Deliver scalable training sessions tailored to customer maturity.

Skills

Onboarding management

Stakeholder management

AI interest

Project management

Customer empathy

Strong communication

Job description

About Plum

Plum is India's leading employee health benefits platform. We cover 600,000 lives across 6,000 companies, growing 80% year on year, cash-flow profitable in FY27, and recently closed our Series B backed by Peak XV, Tiger Global, and Tanglin.

1. The Charter

Insurance in India still remains a hairy problem. No trust. Overcomplicated systems. Too much paperwork. Communication gaps. Commoditisation. Complication. Manual processes. Opacity. Too much fine print. Warped policies. Scamming. Too many hiding features. Loopholes. Fear. Intimidating processes.

Plum is fixing this. The first 30 days are where trust is built or lost. Your job is to make those 30 days exceptional: for every HR admin, and every employee on their team. What we want to build is a seamless, high-touch activation journey for every employer and employee — from the moment they sign with Plum to the end of their first 30 days. Not a support queue. Not a checklist. A red carpet.

Your job is to lead this charter, from vision to execution.

2. Why It Matters for Plum

First impressions are permanent. The first 30 days are when customers decide whether Plum is a vendor or a partner.

When activation is poor, renewals are transactional. When activation is exceptional, customers become advocates — the kind who renew without negotiation and refer without being asked. Every percentage point of activation gain directly compounds into retention, NPS, and revenue.

We believe the Red Carpet Experience is a growth lever, not an operational cost. Done right, it makes our Account Management team's job easier, our support team's job lighter, and our customers' lives genuinely better.

3. What you will do

• Lead the team which will own and manage the onboarding process for our most important customers from pre-sales through successful onboarding closeout


• Partner closely with Account Managers and Insurers to ensure smooth customer handoff experience


• Understand customer goals and successfully manage their onboarding timeline towards value


• Report on metrics and customer feedback to assess the impact of successful onboarding and to help identify new customer initiatives and product opportunities


• Help the team deliver live and scalable training sessions customized to customer maturity and needs


• Understand and consult on product and industry best practices in order to act as a trusted advisor to our customers and inspire new possibilities using our product

Key outcomes you will chase will be the % of customers who achieve the below states in the first 30 days

1. 80%+ Activation

   Employees 'Insurance Ready' — app downloaded, profile complete




2. NPS 80 Advocacy

   Claims NPS target for all first-month claims




3. 3+ Viral Loop

   Employees proactively praising Plum to their HR team

5. We’d love to hear from you if you have:

• Strong problem solving skills (ideal experience of 3+ years at McKinsey, Bain or BCG)


• Total experience of 7-8 years and above


• Team management experience (can run a large team)


• Deep desire to build with AI (some experience is preferred)


• Ability to influence senior stakeholders at both Plum and insurers to deliver for customers


• Very strong written and verbal communication and high numeric ability


• High customer empathy


• Proven project management skills and experience working with multiple customers / on multiple items concurrently