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

Ascend Together is seeking a Sr People Tech Operations Specialist to serve as a Workday SME embedded within the People team. This role is responsible for backend configuration, plan system management, and off-cycle transactions, with a primary specialization in Workday Benefits and Compensation module configuration aligned to partner-firm integrations, plan add-ons, all-company new hires, and open enrollment.

A centerpiece of this role is leading the new Workday Benefits module rollout in partnership with Commit Consulting, and driving the transition off bswift onto a fully Workday-native benefits administration model in close partnership with Total Rewards. Beyond Benefits, the role supports Compensation and career architecture configuration across job profiles and compensation ranges, provides generalist People Tech coverage across the broader HR tech stack, and delegates and monitors delivery from Sentient People Tech resources.

In addition to Workday, we hope this person can expand or come with experience in the Greenhouse software as the overall scope of the People Tech space is expanding to include a Talent focus as well.

An AI-focused development mindset is the connective thread — this Specialist is expected to continuously streamline, automate, and template configuration and testing work to scale capacity rather than headcount as the partner-firm network grows.

Key Relationships

• Reports to: Sr Manager, People Technology
• Key Stakeholders: Total Rewards, People Operations, Partner Firm Heads of People, and IT
• External Partners: Candidates, External Consultants, Vendors

Role Responsibilities

Workday Benefits Implementation (Internal Lead)

• Serve as the internal lead on the new Workday Benefits module implementation alongside Commit Consulting — drive configuration decisions, build, and testing.
• Manage the day-to-day working relationship with Commit Consulting; coordinate scope, timelines, deliverables, and issue resolution.
• Partner with Total Rewards to transition benefits administration off bswift (current ben admin vendor) onto a fully Workday-native model; map parity, validate, and execute cutover.
• Define and execute test plans (unit, parallel, end-to-end); document results and drive defect resolution before go-live.
• Support go-live cutover and post-launch hypercare; stabilize configuration and hand off to steady-state operations.

Workday Benefits Modules (Primary Specialty)

• Own ongoing functional configuration of the Workday Benefits module — plan setup, rates, eligibility rules, and testing.
• Build, test, and drive annual open enrollment in Workday; validate plan/rate setup, event rules, and the employee-facing experience end to end.
• Configure and manage qualifying life events; ensure correct event triggers, eligibility, and downstream processing.
• Configure benefits enrollment for all-company new hires; ensure accurate eligibility, defaults, and enrollment windows.
• Configure new and changing benefit plans and add-ons as the offering evolves; build, test, and deploy with minimal disruption.
• Manage benefit enrollment integrations in Workday; monitor carrier files, troubleshoot errors, and ensure data accuracy.

Absence & Compensation Modules (Secondary Specialty)

• Configure and maintain job profiles, job families, and career architecture in Workday; support job catalog cleanup and standardization across partner firms.
• Build and maintain leave plans, holiday calendars, and associated Absence module functionality
• Build and maintain compensation grades, ranges, and pay range structures; load and validate market data and range updates.
• Configure compensation plans, eligibility rules, and one-time/recurring payment setups; support annual merit and comp review cycles.
• Process and validate off-cycle compensation transactions — adjustments, promotions, and range changes — with audit-ready documentation.

General People & Talent Systems Responsibilities

• Execute Workday system changes for necessary updates; build, test, and deploy.
• Translate policy changes into Workday business process and configuration updates; ensure workflows reflect current policy and approvals.
• Provide core HCM transactional support — M&A integrations, hires, job and org changes, position management, and data corrections.
• Support Greenhouse Recruiting platform with backend configuration needs in partnership with Talent team requirements
• Provide generalist support across the broader HR tech stack in close partnership with Ascend IT and vendors.

Resource Delegation & Vendor Partnership

• Delegate configuration and support tasks to Sentient People Tech resources; monitor delivery quality and timelines and hold the partner accountable to standards.
• Partner with Ascend IT and third-party vendors on system changes, tickets, and enhancements; coordinate dependencies and escalations.

Operational Excellence & Governance

• Maintain testing rigor across all configuration work; build reusable test cases and regression libraries to protect production stability.
• Document configuration, business processes, and SOPs; maintain change logs and knowledge base entries for People Tech.
• Support Workday release readiness (semi-annual updates); assess impact, test new features, and adopt relevant enhancements.
• Identify and build templated, automated, and self-service approaches to recurring configuration to scale through M&A surges.

Education and Experience

• Bachelor's degree in Human Resources, Information Systems, Business Administration, or a related field.
• 4+ years of Workday HRIS configuration experience with deep functional expertise in the Benefits, Compensation and Absence modules.
• Proven ability to manage or lead a Benefits module implementation or major open enrollment cycle in Workday.
• Strong testing discipline: ability to write, execute, and document test cases and manage defect resolution.
• Experience in a PE-backed, multi-entity, or professional services environment preferred.
• Experience supporting Greenhouse Recruiting platform preferred

Knowledge, Skills, and Abilities

• Deep Workday Benefits module expertise — plan setup, eligibility logic, event rules, open enrollment configuration, and carrier integrations.
• Working knowledge of Workday Compensation and career architecture configuration — grades, ranges, job profiles, and comp cycles.
• Exceptional attention to detail and testing rigor; able to build and maintain reusable test frameworks and protect production stability.
• Strong organizational skills — able to manage multiple configuration workstreams, deadlines, and vendor relationships simultaneously.
• Clear communicator with both technical and non-technical stakeholders; comfortable translating policy requirements into system configuration.
• Proactive about documentation; builds SOPs and change logs as a natural part of the work, not as an afterthought.
• Collaborative and adaptable in a fast-growing, multi-entity environment where the playbook continues to evolve.
• Comfortable leveraging AI tools and automation approaches to reduce manual configuration effort and scale team capacity.
• Workday Pro Certification in Benefits or HCM a plus.

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.