Director of Product Engineering

About CalcFocus

CalcFocus is a growing insurtech company delivering cloud-native policy administration and illustration software to the Life & Annuity market. Built on a powerful calculation engine, the company has achieved 100% successful implementations and built a reputation for deep domain expertise, strong product capability, and a genuinely people-first culture.

As CalcFocus enters its next stage of growth, our focus is on expanding market presence while staying grounded in the values that have made the company successful. For more information, visit .

The Opportunity

CalcFocus’s platform powers policy administration and illustration for Life & Annuity carriers, and our calculation engine is a big part of why carriers choose us. As we grow, we’re organizing product development around a clear partnership: Product decides what gets built and why, and Engineering decides how it gets built well. This role is the engineering half of that partnership.

You’ll lead Product Engineering — owning application architecture, capacity planning, and the people and delivery systems that turn a product roadmap into working software. Platform engineers report to you for people management and day-to-day direction; the CTO directs their technical work on committed roadmap items. You’ll partner as a peer with the Director of Product, with the Head of AI on embedding and governing AI through the SDLC, and with Cloud Engineering on how software runs in production.

The team, the product, and the calculation engine are already strong. What doesn’t exist yet is one leader who owns engineering as a function: how it’s structured, how it plans and ships, how its engineers grow, and how its products are architected. This is also a role for someone who has built software from early-stage to scale — who knows what it takes to go from a working product to a mature, extensible platform, and who can do that work in genuine partnership with product management: shaping what gets built, not just receiving requirements, and making the product stronger at every stage of its growth.

We’re looking for someone with a genuine curiosity about both the how and the why of what they’re building. Someone who cares about writing and shipping great software — who is fluent in how AI is changing the way software gets built, and who uses it responsibly and well. And someone who is just as curious about why a solution matters: who wants to understand the business problem well enough that they can look at what’s been built and know whether it actually solves it. In Life & Annuity, that means developing enough intuition about rates, values, and calculation logic that they can tell — before a client does — when something doesn’t look right.

Key Responsibilities

Own the Engineering Function

• Own Product Engineering’s performance, quality standards, and outcomes — answer to the CPO for the health of the function
• Own capacity planning, staffing, and engineering economics — balance quality, speed, and commercial outcome
• Design the operating model: how teams are structured across Application and Platform tracks, how work flows, and how decisions get made
• Set the standard for how AI tooling is used in the engineering org — what’s approved, how it’s governed, and how it improves delivery without cutting corners

Drive the SDLC

• Build and hold the SDLC: definition of done, testing and release gates, documentation standards, and release cadence
• Sign each release on process and quality — alongside the CTO’s architecture and security sign-off
• Make releases trustworthy and predictable

Own Application Architecture & Delivery

• Own application architecture across the product portfolio: how products are designed, how they relate to each other, and how they build on the platform
• Set the delivery standard: code quality, testing, review, documentation, and safe deployment in live carrier environments
• Turn the product roadmap into technical plans and capacity decisions

Build the Team & Its Culture

• Own talent strategy: the hiring profile, what great looks like at every level, and retention
• Develop leaders below you, not just individual contributors
• Sponsor an engineering culture of real feedback, client partnership, high standards, and responsible AI adoption

Make the Partnerships Work

• Partner as a peer with the Director of Product on what gets built, when, and at what quality
• Work closely with the CTO on how products build on the platform — influence through evidence, not authority
• Partner with Cloud Engineering on observability, deployment, and production incidents
• Partner with the Head of AI on embedding AI in the product and SDLC
• Represent engineering in executive client conversations where technical credibility matters

What We're Looking For

Someone who still thinks like an engineer, earns trust through technical judgment, and builds teams people want to stay on.

Six things matter most:

• Engineering function ownership — you’ve owned an engineering org end to end, made the hard calls on people and priorities, and designed how teams are structured and how decisions get made.
• AI-assisted development fluency — you’ve shipped code with AI tooling yourself, or you’ve led engineers doing so and set the standard for how it’s done. You understand what responsible AI adoption in a delivery context actually looks like — not as a policy, but from having done the work.
• Domain curiosity — you become genuinely curious about the business problems your software is solving. In Life & Annuity, that means developing enough intuition about rates, values, and calculation logic that you can look at output and know whether it makes sense for what’s being built. You don’t need to be an actuary — you need to be the kind of person who gets there.
• Application architecture & delivery — you’re deep enough technically to own application architecture and review major design decisions with full context. Java-based enterprise systems, APIs, and data-heavy or calculation-heavy software.
• Team development & engineering culture — you’ve developed leaders, not just ICs. Built a coaching culture with real, timely feedback. Owned hiring and retention for a function.
• Product & platform partnership — you’ve worked as a true peer to product management and alongside an architecture leader who owns the platform. You build cross-functional trust without relying on escalation.

We'd Be Especially Excited If You Have

• Experience building software for Life & Annuity, insurance, or financial services — where domain accuracy in the output is part of the quality bar
• Experience with policy administration, illustration, or actuarial calculation systems
• Experience scaling an engineering team at a growth-stage, PE-backed company
• Experience building on AWS and designing software for observability

Compensation & Benefits

Base salary range: $180,000 – $220,000, anchored to the market for engineering directors at growth-stage software companies.

• Fully remote, with the option to work in office if located in the Philadelphia area
• 401(k) with company match
• Comprehensive benefits for employees and families
• Four weeks of PTO plus company holidays

What It's Like to Work Here

CalcFocus is a people-first company known for its flexible, collaborative, and supportive work environment. Our team is made up of talented, long-tenured employees who stay because they feel valued, trusted, and empowered to do meaningful work. New team members are given the opportunity to learn how we deliver, build relationships, and step into ownership with the support of experienced colleagues.

CalcFocus is an equal opportunity employer committed to building a diverse and inclusive team. We welcome people of all backgrounds, experiences, and perspectives. If you're excited about this role, we encourage you to apply — even if your experience doesn't match every requirement.