Manager – Compensation and Pricing Strategy

About OpenLoop

OpenLoop was co-founded by CEO, Dr. Jon Lensing, and COO, Christian Williams, with the vision to bring care anywhere. Our telehealth support solutions are thoughtfully designed to streamline and simplify go-to-market care delivery for companies offering meaningful virtual support to patients across an expansive array of specialties, in all 50 states.

Commissions are the most personal number in the company. When a plan is unclear or a statement is wrong, reps stop trusting the plan and a plan reps don't trust stops driving behavior. At OpenLoop, we're looking for a Manager of Pricing & Incentive Compensation who owns how we price our offering and how we pay the people who sell it — and makes sure the two reinforce each other.

This is a build-and-run role. You'll own commission administration across the GTM team calculating and issuing statements, resolving disputes, and partnering with Finance on accruals and payroll. You'll also shape what comes next: modeling plan changes, pressure-testing crediting rules before they ship, and moving the cycle off manual spreadsheet work and onto real system logic.

If you're the person who reconciles the number three ways before sending it, and who can explain a payout to a skeptical AE without getting defensive, this role is for you.

Why This Role Exists

OpenLoop's GTM organization has grown quickly, and incentive compensation has grown with it — more plans, more verticals, more crediting scenarios each cycle. Commission administration today is a hands-on process, which means plan design iterates more slowly than the business moves and there's little dedicated capacity for modeling, governance, or automation.

This role creates that capacity. You'll take ownership of the operational cycle — crediting, calculation, statements, disputes, documentation — and become the person GTM leadership and Finance rely on for a defensible answer on any commission question, so plan design decisions get made on data rather than intuition.

What You'll Own

• Commission Calculation & Statements – Run the full commission cycle for the GTM organization: pull and validate closed-won data, apply plan mechanics, calculate payouts, and produce individual statements reps can actually read and reconcile.

• Crediting & Attribution Logic – Own the rules that determine who gets credit for what. Maintain quota and territory assignments, resolve split and multi-rep deals, and adjudicate edge cases against documented plan terms rather than case-by-case judgment.

• Data Integrity & Controls – Validate the commissionable data upstream of every calculation. Identify deal records that will break payout logic, build reconciliation checks between CRM, Finance systems, and payroll, and maintain a clean audit trail for every adjustment.

• Dispute Resolution – Serve as the first line for rep and manager commission questions. Investigate discrepancies, explain the math clearly, and close each inquiry with a documented answer and a fix to the root cause when there is one.

• Plan Design & Modeling Support – Model attainment distributions, payout curves, accelerator scenarios, and cost of sales for proposed plan changes. Flag where a proposed mechanic will be hard to administer, easy to game, or impossible to calculate with the data we have.

• Pricing & Packaging Strategy – Own the structure of how OpenLoop prices and packages its offering across verticals: tier design, bundling, and pricing models (platform fees, per-visit, per-member, minimums). Build the analysis behind every pricing change, including margin impact, competitive positioning, and adoption risk, so decisions rest on data and not anecdote..

• Pricing Performance Analytics – Monitor realized price, discount depth, package mix, and win rates by segment. Turn that data into recommendations for packaging changes, price increases, and renewal pricing..

• Finance & Payroll Partnership – Partner with Finance on accruals, forecasting, and payout files. Deliver commission inputs on the payroll calendar, every cycle, without chasing.

• Systems & Automation – Partner with Revenue Systems to move commission logic out of spreadsheets and into the CRM and reporting layer. Define the field, object, and reporting requirements that make automated commission tracking and self-serve attainment visibility possible.

• Documentation & Governance – Maintain current plan documents, quota records, approved exception logs, and process runbooks so that any calculation can be reproduced and defended six months later.

What We're Looking For

• 5–7 years of experience in commission operations, sales compensation, revenue operations, or FP&A — including ownership of a full commission cycle for a multi-segment GTM team

• Experience designing or materially redesigning incentive plans, not only administering them — you've been in the room where the mechanics get decided

• Advanced spreadsheet skills (Excel and Google Sheets) — complex formula logic, large data sets, and models built to be audited by someone else

• Working knowledge of incentive compensation mechanics: quota, attainment, accelerators, draws, clawbacks, splits, and crediting rules

• Hands-on experience with CRM data (HubSpot and/or Salesforce) — you know where revenue data lives, how it gets dirty, and how to validate it before you use it

• Exceptional accuracy and self-review discipline — you catch your own errors before anyone else does

• Experience owning or materially shaping pricing and packaging decisions in a B2B or SaaS-style business, ideally with multiple buyer segments or revenue models.

• Ability to build pricing models that connect list price, discounting, gross margin, and comp cost into one view of deal economics.

• Clear written and verbal communication with non-analytical audiences; you can explain a payout calculation to a rep, a manager, and a CFO in the language each one needs

• Discretion and judgment with confidential compensation data

• Comfortable in ambiguity — bringing structure to processes that are currently undocumented, and confident holding a position with Sales leadership when the plan terms support it

• SQL, BI tooling (Looker, Tableau), or compensation platform experience (CaptivateIQ, Xactly, Spiff, or similar) is a plus, not a requirement

How We'll Measure Success

• Payout Accuracy – Error rate in issued commission statements, and volume of post-issuance adjustments

• Price Realization – Average realized price against list, and trend in discount depth by segment

• Cycle Timeliness – On-time delivery of statements, payroll files, and accrual inputs against the close calendar

• Dispute Volume & Resolution Time – Number of commission inquiries per cycle and average time to documented resolution, with a downward trend in repeat root causes

• Automation Progress – Share of the commission cycle running on system logic rather than manual spreadsheet work

• Audit Readiness – Ability to reproduce any calculation on request, with complete documentation of plan terms, quota assignments, and approved exceptions

• Stakeholder Trust – Feedback from Sales leadership, Finance, and reps on clarity, responsiveness, and confidence in the numbers

Our Company

We have a relatively flat organizational structure here at OpenLoop. Everyone is encouraged to bring ideas to the table and make things happen. This fits in well with our core values of Autonomy, Competence and Belonging, as we want everyone to feel empowered and supported to do their best work.

Sound like a good fit? We’d love to meet you.