Director of Engineering

Summary

Join PrizePicks, a rapidly growing sports company, as a leader of the Loyalty & Growth engineering team. You will set the technical direction, drive engineering excellence, and partner with various teams to deliver data-driven solutions. Responsibilities include driving experimentation, championing best practices, recruiting and developing engineers, and collaborating with executive leadership. The ideal candidate possesses 10+ years of software engineering experience, including 3+ years in leadership roles, and a deep understanding of user lifecycle strategies. PrizePicks offers a competitive salary, comprehensive benefits, and a flexible work environment.

Requirements

• 10+ years of experience in software engineering, with at least 3 years in engineering leadership roles managing managers and multiple teams
• Proven success leading consumer product engineering teams, particularly in high-growth environments or companies focused on user engagement, growth, or loyalty
• Deep understanding of user lifecycle strategies, growth loops, incentives, and retention mechanics
• Experience working with growth and engagement technology stacks, including tools like RudderStack, Braze, Iterable, Segment, Amplitude, Mixpanel, or similar platforms for campaign orchestration, segmentation, and measurement
• Strong familiarity with event-driven architecture, real-time personalization, and customer data infrastructure
• Strong product mindset — comfortable translating ambiguous business problems into engineering-led solutions that move the needle
• Track record of building inclusive, high-performing engineering teams with strong focus on talent development and psychological safety
• Ability to thrive in fast-paced environments with changing priorities, balancing strategic thinking with a hands-on leadership style
• Excellent communicator and collaborator who can influence cross-functional stakeholders and executive teams alike

Responsibilities

• Lead and scale the engineering organization for the Loyalty & Growth team, setting the technical direction and driving engineering excellence across multiple squads
• Partner with Product, Marketing, Data, and Design to define the roadmap and deliver scalable, data-driven solutions that optimize acquisition, onboarding, retention, referrals, rewards, and lifecycle engagement
• Drive experimentation at scale — lead initiatives to test and iterate on loyalty programs, promotional mechanics, and personalization using A/B testing and modeling
• Champion best practices in software architecture, design, and coding to ensure long-term speed and quality across consumer-facing experiences
• Recruit, coach, and grow exceptional engineers and engineering managers. Build a culture of empowerment, accountability, and continuous learning
• Collaborate with executive leadership to align engineering initiatives with company-wide growth goals and deliver measurable business outcomes
• Implement scalable processes for planning, estimation, execution, and delivery across multiple initiatives simultaneously
• Foster a strong engineering culture centered on innovation, velocity, ownership, and cross-functional collaboration

Benefits

• Company-subsidized medical, dental, & vision plans
• 401(k) plan with company match
• Annual bonus
• Flexible PTO to encourage a healthy work/life balance (2 weeks STRONGLY encouraged!)
• Generous paid leave programs, including 16-week paid parental leave and disability benefits
• Workplace flexibility and modern work schedules focused on getting the job done, not hours clocked
• Company-wide in-person events and team outings
• Lifestyle enhancement program
• Company equipment provided (Windows & Mac options)
• Annual performance reviews with opportunities for growth and career development