The roleSierra is hiring a Sales Compensation expert to own the design, modeling, and administration of compensation programs across the GTM organization. You will build the compensation infrastructure that motivates a world-class sales team and keeps Sierra's incentive structures tightly aligned with how the business creates value.
Sierra's commercial model includes outcome-based pricing, a paid POC phase, and multi-year enterprise contracts, each of which creates nuances that standard compensation frameworks don't handle well. You will need to think from first principles about how to structure incentives that drive the right behaviors across a global and growing GTM team, from initial close through POC delivery, expansion, and renewal.
What you'll do- Own the end-to-end design and annual refresh of compensation plans across Account Executives, Sales Engineers, and other GTM roles, facilitating alignment across GTM Operations, Finance, and HR
- Build compensation frameworks from first principles that reflect Sierra's unique commercial model-outcome-based pricing, paid POC conversion, and multi-year enterprise contract structures
- Develop and maintain the financial models that project cost and attainment impact of plan design choices before any plan goes to the field
- Track in-year compensation performance, identify design gaps and anomalies, and surface insights that inform ongoing plan adjustments
- Own compensation policy and documentation-ensuring reps and managers have clarity on how their plans work at all times
- Partner with Finance on expense planning and accruals, and with HR on benchmarking, leveling, and the relationship between base and variable compensation
What you'll bring- Deep expertise in sales compensation design and administration at an enterprise B2B software or AI company, across a range of GTM roles and plan types
- Strong financial modeling skills; comfortable owning compensation models at the level of precision Finance expects
- Genuine design thinking applied to compensation-able to identify when a plan creates unintended incentives and fix it before it hits the field
- Clear and direct communicator who can explain compensation mechanics to a sales rep, a CFO, and a new hire in equal measure
- Collaborative by nature-this role touches Finance, HR, Legal, and GTM leadership, and success depends on strong relationships across all of them
- Comfortable with ambiguity; helps write the playbook rather than waiting for one to exist
Even better...- Experience with outcome-based, usage-based, or consumption pricing models
- Experience designing compensation plans across global geographies
What we offerWe want our benefits to reflect our values and offer the following to full-time employees:
- Flexible (unlimited) paid time off
- Medical, dental, and vision benefits for you and your family
- Life insurance and disability benefits
- Retirement plan dependent on country of employment
- Parental leave
- Fertility and family building benefits through Carrot
- Lunch, as well as delicious snacks and coffee to keep you energized
- Discretionary benefit stipend giving people the ability to spend where it matters most
- Free alphorn lessons
