Senior Product Manager, Paychex, Inc., Rochester, NY February 2014 – January 2020 Directed management of all insurance-related products including health insurance, FSA, COBRA, benefit administration, ACA, P&C and related products totaling $260M+ annual revenue Grew revenue to $45M/year over 2 years by leading development, launch and distribution of ACA reporting product Eliminated $18M in sales expense and saved unaware clients from heavy IRS penalties by proactively onboarding nearly 9,000 clients onto ACA service Eliminated $500K in expense by collaborating with Compliance and Operations to furnish nearly all IRS ACA forms online Lead development of new online health insurance enrollment app, increasing adoption from 4% to over 20% in 1 year Increased investment in development of benefits administration platform 50% by securing approval of the business case
Product Manager, Paychex, Inc., Rochester, NY April 2007 – February 2014 Led product management and strategy for health insurance agency and related businesses. Oversaw carrier evaluation and onboarding Conducted market research to understand reasons for high client losses Headed cross-functional task force to address performance issues identified by market research Proposed implementation of changes to executive leadership and initiated implementation of changes, leading to Agency reorganization, numerous process and policy improvements and a 35% reduction in YOY client loss rate. Led integration with SaaS benefit account provider to replace obsolete FSA platform, resulting in a 25% reduction in YoY client loss rate
Skills Required
- Experience in insurance-related product management
- Strong leadership and cross-functional collaboration skills
- Proven experience in market research and product strategy
- Ability to manage and direct large revenue streams
- Experience with SaaS and online applications
SquarePeg Hires Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about SquarePeg Hires and has not been reviewed or approved by SquarePeg Hires.
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Healthcare Strength — Public role descriptions cite medical, dental, and vision coverage, including one stating 100% employer-paid premiums for employees and 75% for dependents. These signals point to robust healthcare offerings in at least some postings.
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Retirement Support — Some listings specify a 401(k), with one noting a 4% company match. This suggests meaningful retirement support is included in certain contexts.
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Leave & Time Off Breadth — Multiple postings reference “Responsible Time Off” or unlimited PTO. This indicates broad time-off flexibility.
SquarePeg Hires Insights
What We Do
SquarePeg is a job matching service for both employers and candidates, which aims to bring better predictive data to job search, reducing reliance on resumes, referrals and job posts. We built custom online assessments for candidates that identify a range of skills, character traits and aptitudes, and matching them with the unique predictors of performance for individual companies. We are focusing on non-technical roles. As a service for employers, SquarePeg conducts the search using its own database and algorithm, and provides clients with curated lists of candidates which are high potential matches.








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