Straddle is solving foundational problems in an $80 trillion market: building account-to-account payments that are faster, more reliable, and more cost-effective than card networks. We're scaling rapidly and have raised a $6.5M seed round from leading investors including Bonfire Ventures, Kickstart Fund, and Veridical Ventures. We are now seeking an experienced, hands-on VP of Engineering to join our leadership team and spearhead the next phase of our platform's development and scale.

In this pivotal role, you will not only lead and scale our engineering organization of 8 dedicated engineers but also remain deeply hands-on, writing code, architecting systems, and making critical technical decisions daily. You will be instrumental in evolving Straddle’s innovative payments infrastructure, ensuring it is robust, scalable, and secure, directly contributing to our mission of modernizing money movement.

Your impact

As VP of Engineering, you'll architect the next-generation of payments and scale the engineering organization that powers it. Working directly with the founders in Denver, CO, you'll be empowered to shape both what we build and how we build it, translating ambitious vision into hyper-scaled, resilient infrastructure. This is a unique opportunity to build a foundational platform from its early stages, embed your technical DNA into our systems, and create the backbone that will process billions in payments.

What you'll do

• Lead, mentor, and scale a world-class engineering team from 8 to 20+ engineers, fostering a culture of craft, ownership, continuous learning, and pragmatic problem-solving.

• Design, code, and architect core platform systems—from bank integrations and real-time payment processing to scalable API architecture and client-side applications—setting the standard for engineering excellence through your own contributions.

• Define and drive Straddle’s overarching engineering strategy, skillfully balancing rapid iteration for market responsiveness with the crucial need for long-term scalability and reliability.

• Establish, champion, and refine engineering best practices across the entire development lifecycle—from robust code reviews and comprehensive testing methodologies to effective incident response protocols—ensuring both high development velocity and unwavering system quality.

• Partner closely with the founders and product leadership to translate ambitious business objectives and customer needs into actionable technical roadmaps and resilient architectural designs.

What you bring

• 8+ years of progressive experience in building and scaling high-availability, high-growth systems, with at least 3+ years in a significant leadership role managing and mentoring engineering teams, preferably within fintech, SaaS, or API-first companies.

• Deep, hands-on expertise in architecting, developing, and maintaining complex, distributed systems using enterprise-grade languages (e.g., C#/.NET Core, Java, Go) and modern software development practices.

• Proven ability as a hands-on technical leader, comfortable and adept at writing production-quality code, conducting insightful code reviews, and guiding critical architectural decisions for teams of 5-30+ engineers.

• Mastery of cloud infrastructure, preferably Azure (or AWS/GCP), including infrastructure-as-code (e.g., Terraform), containerization technologies, and sophisticated cost optimization strategies at scale.

• A strong, ingrained security-first mindset, with practical, demonstrable experience in implementing robust security best practices, data protection measures, and ensuring compliance in financial services or similarly regulated environments.

• Exceptional ability to articulate and communicate complex technical concepts, strategies, and decisions clearly, persuasively, and with impact to both technical and non-technical audiences, in written and verbal forms.

• Demonstrated success and adaptability operating effectively in a fast-paced, dynamic startup environment, comfortable with ambiguity, fostering clarity, and driving rapid iteration.

Nice-to-haves

• Direct experience with various payment rails (e.g., ACH, RTP, FedNow, Card Networks) and a solid understanding of the payment processing ecosystem.

• Background in fintech APIs, open banking standards, financial data aggregation platforms, or payment orchestration systems.

• In-depth knowledge of distributed systems patterns, event sourcing, domain-driven design, and microservices (without going overboard!)

• A track record of building intuitive and robust developer-facing APIs and SDKs that delight engineers.

You'll thrive here if...

• You are passionate about architecting and building highly reliable, scalable, and secure systems, and possess a genuine interest in innovating within the fintech and payments space.

• You lead by example, are not afraid to roll up your sleeves and dive deep into code and complex architectural challenges, and fundamentally believe in shipping production-quality work.

• You excel at "raising the floor" by empowering every engineer to be significantly more productive through thoughtful mentorship, the implementation of superior tooling, and the creation of clear, elegant system abstractions.

• You think in systems, constantly identifying opportunities for leverage and building robust platforms and frameworks that enable small, highly focused teams to achieve an outsized impact.

• You are an intentional and transparent communicator, capable of crafting clear technical strategies and decisions that align the team and drive focus without unnecessary bureaucracy.

• You naturally thrive in a dynamic startup environment, adept at creating clarity amidst ambiguity and moving decisively and quickly in partnership with cross-functional teams.

Maybe not a fit if...

• You prefer highly established, large corporate environments with deeply entrenched processes and a more hands-off approach to technical leadership.

• You are primarily seeking a purely managerial role, without the expectation of significant day-to-day coding, direct architectural design, and substantial individual technical contribution.

• You are less comfortable with the inherent pace, constant evolution, and high degree of adaptability required in an early-stage company that is aggressively scaling its operations and impact.

• You would rather manage projects and teams from a distance than be deeply embedded in the technical trenches, collaboratively solving challenging problems alongside your team.

Why Straddle?

• Mission Impact: This is an opportunity to build critical financial infrastructure that will fundamentally change how money moves in the US, making it faster, more reliable, and more accessible for millions of businesses.

• Technical Challenges: Engage with and solve hard distributed systems problems at the fascinating intersection of modern cloud architecture and legacy banking systems, pushing the boundaries of what's possible in payments.

• Ownership & Upside: Receive a significant equity stake in a rapidly growing, well-funded company with proven product-market fit, and have the autonomy to shape our core technical direction and future.

• Team & Culture: Work alongside a talented, ambitious, and low-ego team that deeply values clear thinking, direct and honest communication, and the craft of shipping high-quality, impactful code.

• Growth Trajectory: Join us at a perfect inflection point—we have a validated product, strong financial backing, and massive headroom to innovate and scale, offering unparalleled growth opportunities.

• Benefits: We offer a competitive base salary, meaningful equity, a full benefits package, unlimited PTO (with a 4-week minimum encouraged), an equipment budget, a $2,500 annual home office stipend, and relocation assistance to join our team in Denver, CO.

Ready to Join?

If you’re excited about the challenge of building the next generation of payment infrastructure and fundamentally transforming how businesses transact, we'd love to hear from you.

Apply by sending your resume and a note about the most complex system you've architected and scaled to careers@straddle.io with "VP Engineering" in the subject line.

Straddle is an equal opportunity employer committed to building a diverse and inclusive team.