About Ascend Ascend empowers entrepreneurial CPAs to reach their goals with an innovative growth model that brings their firms into the new age. Backed by PeopleFirst private equity firm Alpine Investors (~$20B AUM), Ascend is the leading aggregator of regional accounting firms in the U.S., with ~2,800 employees globally and approaching $1B in revenue. Ascend has built a modern platform for regional accounting firms that enables them to stay independent in their brand, approach to client service, and cultural autonomy, while benefiting from the strategic support and resources of a large CPA firm. Ascend provides access to growth capital, a robust talent acquisition engine, best-in-breed technology, AI tools, shared back-office services, and modernized growth incentives, so firms can surmount the typical standalone partnership model challenges and reach their full potential. Founded in January 2023, Ascend has experienced rapid growth both organically and through M&A, having completed ~45 acquisitions to date, placing it in the Top 25 largest accounting firms in the U.S. For more information, visit ascendtogether.com. About Alpine Investors Alpine Investors is a PeopleFirst private equity firm committed to building great companies by working with, learning from, and developing exceptional people. Alpine prides itself on fostering cultures where people value empowerment, diversity, fairness, integrity, and intellectual honesty. Founded in 2001, Alpine specializes in investments in companies in the software and services industries. Alpine has ~$20 billion in AUM and has offices in San Francisco, New York, Salt Lake City, and Austin, TX. For more information on the firm, visit www.alpineinvestors.com. Position Summary Jackson Thornton, a partner firm within the Ascend ecosystem, is seeking a Benefits Analyst to own the day-to-day administration and strategic oversight of the firm's self-funded health and wellness plans, all employee leave programs, and COBRA administration. This individual will serve as the primary point of contact between Jackson Thornton, its third-party administrator (TPA), stop-loss carrier, and benefits vendors — ensuring seamless plan operations, regulatory compliance, and a positive member experience across the firm's growing employee base. A critical part of this role is leading benefits integration efforts as new Partner Firms join the Ascend platform. This person will manage the full transition of incoming employees onto Jackson Thornton's plans, partnering closely with the broker, carriers, and People Operations team to ensure every new employee lands with no gaps in coverage and a clear, welcoming benefits experience. This is a high-ownership, high-visibility role for a detail-oriented benefits professional who thrives in a fast-paced, multi-entity environment and takes genuine pride in serving employees well. The Benefits Analyst will report to the Head of People and be positioned as Jackson Thornton's internal Benefits Administration function. Key Relationships Reports to Head of People at Jackson Thornton (with dotted line to Sr Manager, Total Reward at Ascend) Key Stakeholders Employees, People Operations team, Finance & Accounting, Payroll, and Partner Firm HR contacts External Partners Third-party administrator (TPA), stop-loss carrier, pharmacy benefit manager, benefits broker, and wellness vendors Role Responsibilities Health & Wellness Plan Administration Manage open enrollment, new hire enrollments, qualifying life events, and dependent verification; maintain accurate eligibility records Monitor claims processing with the TPA; review claims reports, escalate issues, and ensure timely resolution of member inquiries Serve as primary liaison with the TPA, stop-loss carrier, pharmacy benefit manager, and wellness vendors; manage contracts and SLAs Develop and distribute benefits communications including plan summaries, open enrollment materials, and policy updates; serve as the go-to resource for all employee benefits questions Partner with the broker to conduct annual plan design reviews, benchmarking, and cost modeling for self-funded arrangements Administer COBRA qualifying events, generate and distribute election notices, track election periods and premium payments, coordinate with the TPA for continuation coverage, and ensure timely compliance with all COBRA notification requirements Manage the performance of benefits administration software, ensuring a smooth and accurate enrollment experience for employees and administrators Generate and maintain enrollment and cost reports for Jackson Thornton functional teams and the broker Leave Management Process FMLA requests, track entitlements, manage certifications, and coordinate with payroll for unpaid leave periods Coordinate the interactive process for ADA accommodation requests; document outcomes and ensure compliance Monitor and ensure compliance with applicable state and local leave mandates, including paid family leave and sick leave laws Maintain accurate leave balances, generate utilization reports, and flag potential concerns for leadership review Financial Oversight Track plan expenditures against the annual budget; flag variances and recommend corrective actions Coordinate with the stop-loss carrier on specific and aggregate claims; manage the reimbursement process Review and approve TPA, pharmacy, and vendor invoices; resolve billing discrepancies Prepare cost trend analyses, per-member-per-month reports, and renewal projections for leadership review Compliance & Reporting Ensure plan compliance with ERISA, ACA, HIPAA, COBRA, PCORI, and other applicable federal and state regulations Prepare and submit required government filings including Form 5500, SAR, ACA reporting (1094-C / 1095-C), and RXDC reporting; coordinate all required participant distributions Review updated plan documents and SPDs from carriers; ensure all materials are current and accessible to plan participants; update internal SOPs to reflect regulatory and plan changes Maintain organized records and documentation to support internal and external audits Partner Firm Integrations & Onboarding Lead the benefits integration process when new Partner Firms join Ascend; partner with the broker to assess existing plans, map transition timelines, and coordinate enrollment into Jackson Thornton's benefits programs Work with incoming firms' prior carriers and TPAs to obtain census data, verify eligibility, and ensure seamless enrollment of all new members with no gaps in coverage Evaluate incoming firms' plan designs against Jackson Thornton's offerings; identify differences, develop transition communications, and manage employee expectations during changeover Coordinate with the TPA, stop-loss carrier, and all carriers to add new groups, update contracts, and ensure system readiness for incoming populations Develop and deliver tailored onboarding materials, host benefits orientation sessions for incoming employees, and serve as the primary point of contact throughout the transition period Education and Experience Bachelor's degree in Human Resources, Business Administration, or a related field 5+ years of progressive benefits administration experience, including hands-on management of self-funded health plans Demonstrated experience with COBRA, FMLA, ADA accommodations, and multi-state leave compliance Prior experience managing benefits integrations in an M&A or multi-entity environment strongly preferred Familiarity with benefits administration platforms and HRIS systems; experience with government filings (Form 5500, ACA reporting) a strong plus Knowledge, Skills, and Abilities Deep familiarity with Blue Cross Blue Shield plans, including plan structures, network configurations, and carrier-specific processes for enrollment, claims, and escalations. Deep technical knowledge of self-funded health plan administration, stop-loss arrangements, and the regulatory landscape (ERISA, ACA, HIPAA, COBRA, PCORI) Exceptional attention to detail and organizational skills — able to manage multiple workstreams, deadlines, and vendors simultaneously without letting things fall through the cracks Strong employee-facing communication skills warm, clear, and confidence-inspiring when helping employees navigate benefits questions, especially during enrollment or life events Analytical mindset — comfortable working with cost reports, utilization data, and plan financials to identify trends and inform decision-making Proactive compliance orientation stays current on regulatory changes and proactively updates processes and documentation before issues arise Collaborative and adaptable in a fast-growing, multi-entity environment where the playbook continues to evolve Proficient with Microsoft Office Suite (particularly Excel); experience with benefits administration software and HRIS platforms required What You Can Count on at Ascend We live by our values Own it. We seize growth opportunities with the passion, speed, and accountability of an entrepreneur. Serve wholeheartedly. We love our people and serve them with positivity and kindness. Be excellent. We set a high bar because our mission matters. Win together. We stay in sync, achieve as a team, and celebrate each other. Bring the sunshine. We have fun and bring enthusiasm to make the journey joyful. Compensation and Other Highly competitive cash and equity bonus compensation package, including attractive benefits. Start date is as soon as practicable. At Ascend, we provide a fair and equal employment opportunity for all candidates regardless of race, color, religion, national origin, gender, pregnancy, sexual orientation, gender identity/expression, age, marital status, disability, or any other legally protected characteristic. Ascend hires and promotes individuals solely based on qualifications for the position to be filled and business needs. Apply To This Job