Client Experience Delivery Lead
Top Benefits
About the role
WHO ARE WE?
Oliver is a data and CX product company modernizing how group benefits and pensions are managed across North America.
Our intelligent platform empowers unions, trust funds, employers, and members to administer benefits with greater transparency, accuracy, and control. We work with brokers, TPAs, MGAs, insurers, and consultants to power smarter administration, automation, and user experiences.
Oliver is redefining the benefits experience — and we’re looking for educators, communicators, and product champions to join the journey.
YOUR ROLE
As the Client Experience & Delivery Lead, you will be the operational and strategic lead a high-value portfolio of clients.
You’ll own end-to-end delivery, product adoption, and client engagement — ensuring that every interaction delivers measurable value. With a focus on depth rather than breadth, you’ll work closely with clients to strengthen relationships, drive operational excellence, and support growth opportunities.
This role is ideal for someone who thrives in high-touch environments, enjoys problem-solving across teams, and wants to make a visible impact on both client success and internal process improvements.
YOUR IMPACT
Client Delivery & Engagement
- Own delivery of client projects, support tickets, and product rollouts for a focused set of accounts.
- Serve as the single point of contact for client communications, planning, and issue resolution.
- Maintain day-to-day operational oversight, ensuring delivery quality, timeliness, and budget adherence.
Growth & Revenue Enablement
- Identify upsell and cross-sell opportunities aligned to client needs and product enhancements.
- Partner with Sales on renewal discussions and expansion planning.
- Deliver data-driven QBRs showcasing ROI, performance trends, and future opportunities.
Financial Accountability
- Act as cost center owner for assigned clients, maintaining accuracy.
- Track profitability, forecast renewals, and flag potential revenue or cost risks.
- Collaborate with Finance on forecasting and margin analysis.
Product Collaboration
- Represent the client’s voice in roadmap discussions and feedback loops.
- Coordinate rollout and adoption of new product features across your accounts.
- Partner with Support and Product to ensure readiness for upcoming releases.
Operational Excellence
- Triage and resolve inbound client requests based on urgency and impact.
- Identify process gaps and recommend workflow improvements.
- Track delivery performance across SLA adherence, ticket resolution, and client satisfaction.
CAREER GROWTH AND DEVELOPMENT
This role is a development pathway toward:
- Senior Manager, Client Experience & Delivery
- Engagement Lead or Client Operations Director
- Cross-functional roles in Product, Strategy, or Revenue Operations.
At Oliver, we invest in your growth — through mentorship, learning programs, and the opportunity to take on broader strategic responsibilities over time.
THIS IS YOU
Experience:
- 3–5 years of experience in client success, account management, or delivery/project management.
- Proven success managing multiple workstreams for enterprise or high-value clients.
- Strong financial acumen — comfortable with budgeting, forecasting, and reporting.
- Experience with CRM, ticketing, and project management platforms.
- SaaS, benefits administration, or insurance industry experience is an asset.
Certifications (Preferred):
- PMP, PRINCE2, or CAPM certification.
- Customer Success or Account Management certification is an advantage .
Your Skills & Attributes:
- Exceptional communicator who can build trust across functions.
- Analytical thinker who can translate performance data into insights and actions.
- Adept at managing competing priorities and tight timelines.
- Collaborative and solutions-oriented mindset.
Decision-Making Authority Level:
- Decision maker for day-to-day client delivery, renewals, and account-level budgets.
- Recommends strategies for growth, operational improvements, and product alignment.
YOUR COMPENSATION & BENEFITS
At the time of this posting, the estimated annual base salary pay range for this position is $70,000k -$75,000k. This range reflects the annual base salary only pay and does not encompass our comprehensive total rewards, benefits, and potential bonuses that we proudly offer.
Perks & Benefits:
- Flexible Work Arrangements – Remote-first culture with optional in-person collaboration.
- Comprehensive Health & Wellness Programs – Medical, dental, vision, and mental health support.
- Professional Development Support – Training programs, certifications, and mentorship.
- Paid Time Off – Generous vacation, sick days, and personal leave.
- Retirement Savings Plan – Employer-matching RRSP contributions.
WHAT YOU'LL GET
Oliver’s purpose is to empower success, propel evolution, and ignite innovation for the future. We believe in fostering an inclusive culture supported by our core values: Integrity and Care, Simplicity, Continuous Learning and Growth, and Design Success.
Join us in shaping the next generation of benefits administration technology.
About Oliver Insurance Software
Oliver Insurance Software was created by CDAT Software over 40 years ago to build bespoke pension and benefits technology solutions for clients. Since that time we’ve been serving clients from small, single employers to large multi-employer groups, trusteed and insured plans. Some of our clients have been with us since the very beginning.
More recently CDAT became Oliver Insurance Software; a modern, scalable, highly configurable solution designed to better serve our clients and the broader health and life insurance, benefits and pension administration market across North America.
Today, Oliver provides comprehensive, modern life insurance, health benefits and pension administration software. We continue to keep our clients’ needs at the core of everything we do and are driven by a shared desire to create the most comprehensive administrative software solution on the market.
Client Experience Delivery Lead
Top Benefits
About the role
WHO ARE WE?
Oliver is a data and CX product company modernizing how group benefits and pensions are managed across North America.
Our intelligent platform empowers unions, trust funds, employers, and members to administer benefits with greater transparency, accuracy, and control. We work with brokers, TPAs, MGAs, insurers, and consultants to power smarter administration, automation, and user experiences.
Oliver is redefining the benefits experience — and we’re looking for educators, communicators, and product champions to join the journey.
YOUR ROLE
As the Client Experience & Delivery Lead, you will be the operational and strategic lead a high-value portfolio of clients.
You’ll own end-to-end delivery, product adoption, and client engagement — ensuring that every interaction delivers measurable value. With a focus on depth rather than breadth, you’ll work closely with clients to strengthen relationships, drive operational excellence, and support growth opportunities.
This role is ideal for someone who thrives in high-touch environments, enjoys problem-solving across teams, and wants to make a visible impact on both client success and internal process improvements.
YOUR IMPACT
Client Delivery & Engagement
- Own delivery of client projects, support tickets, and product rollouts for a focused set of accounts.
- Serve as the single point of contact for client communications, planning, and issue resolution.
- Maintain day-to-day operational oversight, ensuring delivery quality, timeliness, and budget adherence.
Growth & Revenue Enablement
- Identify upsell and cross-sell opportunities aligned to client needs and product enhancements.
- Partner with Sales on renewal discussions and expansion planning.
- Deliver data-driven QBRs showcasing ROI, performance trends, and future opportunities.
Financial Accountability
- Act as cost center owner for assigned clients, maintaining accuracy.
- Track profitability, forecast renewals, and flag potential revenue or cost risks.
- Collaborate with Finance on forecasting and margin analysis.
Product Collaboration
- Represent the client’s voice in roadmap discussions and feedback loops.
- Coordinate rollout and adoption of new product features across your accounts.
- Partner with Support and Product to ensure readiness for upcoming releases.
Operational Excellence
- Triage and resolve inbound client requests based on urgency and impact.
- Identify process gaps and recommend workflow improvements.
- Track delivery performance across SLA adherence, ticket resolution, and client satisfaction.
CAREER GROWTH AND DEVELOPMENT
This role is a development pathway toward:
- Senior Manager, Client Experience & Delivery
- Engagement Lead or Client Operations Director
- Cross-functional roles in Product, Strategy, or Revenue Operations.
At Oliver, we invest in your growth — through mentorship, learning programs, and the opportunity to take on broader strategic responsibilities over time.
THIS IS YOU
Experience:
- 3–5 years of experience in client success, account management, or delivery/project management.
- Proven success managing multiple workstreams for enterprise or high-value clients.
- Strong financial acumen — comfortable with budgeting, forecasting, and reporting.
- Experience with CRM, ticketing, and project management platforms.
- SaaS, benefits administration, or insurance industry experience is an asset.
Certifications (Preferred):
- PMP, PRINCE2, or CAPM certification.
- Customer Success or Account Management certification is an advantage .
Your Skills & Attributes:
- Exceptional communicator who can build trust across functions.
- Analytical thinker who can translate performance data into insights and actions.
- Adept at managing competing priorities and tight timelines.
- Collaborative and solutions-oriented mindset.
Decision-Making Authority Level:
- Decision maker for day-to-day client delivery, renewals, and account-level budgets.
- Recommends strategies for growth, operational improvements, and product alignment.
YOUR COMPENSATION & BENEFITS
At the time of this posting, the estimated annual base salary pay range for this position is $70,000k -$75,000k. This range reflects the annual base salary only pay and does not encompass our comprehensive total rewards, benefits, and potential bonuses that we proudly offer.
Perks & Benefits:
- Flexible Work Arrangements – Remote-first culture with optional in-person collaboration.
- Comprehensive Health & Wellness Programs – Medical, dental, vision, and mental health support.
- Professional Development Support – Training programs, certifications, and mentorship.
- Paid Time Off – Generous vacation, sick days, and personal leave.
- Retirement Savings Plan – Employer-matching RRSP contributions.
WHAT YOU'LL GET
Oliver’s purpose is to empower success, propel evolution, and ignite innovation for the future. We believe in fostering an inclusive culture supported by our core values: Integrity and Care, Simplicity, Continuous Learning and Growth, and Design Success.
Join us in shaping the next generation of benefits administration technology.
About Oliver Insurance Software
Oliver Insurance Software was created by CDAT Software over 40 years ago to build bespoke pension and benefits technology solutions for clients. Since that time we’ve been serving clients from small, single employers to large multi-employer groups, trusteed and insured plans. Some of our clients have been with us since the very beginning.
More recently CDAT became Oliver Insurance Software; a modern, scalable, highly configurable solution designed to better serve our clients and the broader health and life insurance, benefits and pension administration market across North America.
Today, Oliver provides comprehensive, modern life insurance, health benefits and pension administration software. We continue to keep our clients’ needs at the core of everything we do and are driven by a shared desire to create the most comprehensive administrative software solution on the market.