Principal Software Engineer

POS-33300

About the Team

[in-office, hybrid, and remote] 

HubSpot's Adaptive Monetization group owns the systems that determine how customers buy, contract, and pay for HubSpot — at scale, with direct financial consequence. Our infrastructure handles usage metering, contract orchestration, and subscription lifecycle management for every customer on the platform. An outage here doesn't just affect user experience; it blocks customers from purchasing HubSpot entirely, and bugs typically produce immediate, measurable financial impact.

We're in the middle of a multi-year shift to transform HubSpot's straight-line SaaS subscription model and replace it with a flexible contracting layer that can support usage-based billing, commit-based pricing, and enterprise-grade contract structures. This work has executive visibility and is directly tied to HubSpot's revenue growth and ships meaningful impact to our customers.

The core team for this role is roughly 15 engineers across 3 focused team, with an additional influence and impact radius that extends across approximately 180 engineers in the broader Fintech organization.

About the Role

We're looking for a Principal Software Engineer to help architect, build, and influence the evolution of HubSpot’s monetization model and strategy — and to do it incrementally, on a system that is live and load-bearing every day.

This is a hands-on technical role. Approximately 70-80% of your time will be spent writing code, leading designs, reviewing architectures, and owning technical direction on some of the most complex systems at HubSpot. The remainder will be split between cross-functional strategy, mentoring, and building technical credibility across the broader fintech engineering organization.

This is not a greenfield opportunity. The ideal person is someone who finds genuine satisfaction in making a complex, mission-critical legacy system incrementally better — and who can bring others along on that journey. If you've thrived at a publicly traded fintech company navigating the intersection of audit rigor, product velocity, and distributed systems complexity, this role was written for you.

What You'll Do

Architect the future of HubSpot's contract and monetization layer

• Lead the technical strategy for moving HubSpot from a fixed SaaS subscription model to a flexible contracting platform that supports usage-based, commit-based, and enterprise-grade pricing structures.
• Define and own the core architecture for contract lifecycle management, usage metering, entitlement enforcement, and pricing model extensibility — using our internal Corex contract orchestration framework as the foundation.
• Make principled tradeoffs between correctness, compliance, and product velocity in a system where the stakes are financial.

Be a deeply hands-on, high-leverage builder

• Write production code regularly. Lead design reviews. Own large initiatives end-to-end, from architecture through rollout.
• Drive multi-team technical efforts that span the three squads within Adaptive Monetization and require coordination across the broader fintech organization.
• Turn ambiguity into clear technical direction and working software — and stay hands-on throughout.

Navigate complexity without creating it

• Incrementally improve systems that cannot be rewritten from scratch. HubSpot's current contract infrastructure is load-bearing; this work requires surgical precision, not clean-slate thinking.
• Bring the team with you — identifying paths forward that are safe to ship incrementally while maintaining reliability.
• Raise the bar on resilience and observability in a system that generates dozens of production pages per day as the business shifts toward new pricing models.

Communicate with clarity across the organization

• Translate deeply technical architectural decisions for finance, compliance, legal, and executive stakeholders. This role requires you to operate effectively in rooms where the other people are not engineers.
• Influence the product roadmap by helping leadership understand technical tradeoffs between speed, correctness, and long-term platform health.
• Represent the engineering perspective on pricing strategy, contract flexibility, and go-to-market changes that require systems changes to support.

Grow the fintech engineering organization

• Mentor senior and staff engineers within Adaptive Monetization and across the broader Fintech org.
• Partner with your peers — including the other Fintech principal engineers — to align on patterns that reduce complexity and increase reliability across the organization.
• Participate in recruiting and help raise the hiring bar for technical talent in the fintech space.

What You Bring

• Proven experience designing and evolving distributed systems with strict financial correctness requirements — billing infrastructure, payment processing, contract management, usage metering, or similar.
• A background at a publicly traded company where audit rigor, compliance constraints, and real-money consequences shaped the way you built software. Engineers from Stripe, Block, Adyen, PayPal, or similar environments tend to arrive with the right instincts for this work.
• The ability to operate effectively on complex, legacy systems that cannot be paused or rewritten — you know how to make progress incrementally while protecting reliability.
• Strong executive communication skills. You can walk a CFO or compliance officer through a technical architecture decision, adapt the framing to what they care about, and leave the room with alignment.
• A mentorship orientation. You're someone junior engineers seek out, and you measure your impact in part by how much better the engineers around you get.
• Comfort with ambiguity. The system this role is responsible for is changing faster than it was designed to handle. You'll receive a lot of signal and need to make good decisions quickly.
• Deep backend engineering expertise. This is not a platform, DevEx, or infrastructure role — the work is in the financial logic, data models, and service contracts that power HubSpot's monetization.

Why This Role Matters

HubSpot's ability to offer commit-based enterprise contracts, charge based on usage, and compete for the largest, most complex customers in the market depends entirely on the contracting and monetization infrastructure this role will help build. This is multi-year work with direct revenue consequence and executive visibility — and the person who leads the technical architecture of this system will have a meaningful impact on what HubSpot can sell, and to whom, for years to come.