Head of Engineering



Software Engineering
United States · Remote
Posted on Wednesday, April 10, 2024

Who We Are

Settle is on a mission to make buying inventory super easy. Since the company’s inception in 2019, we’ve been building a cashflow management platform that allows founders and small business owners to more easily manage their company’s financial health with a mix of accounts payable and flexible financing tools. We already work with some amazing brands that you probably know and love, like Starface, Ghia, and Italic.

Check us out in On Deck's Top Companies of 2023, Forbes' Next Billion-Dollar Startups, Techcrunch and this Kleiner blog post.

About the role:

As the Head of Engineering, you will play a pivotal role in leading our engineering team by fostering a strong culture across remote teams, driving product innovation, and ensuring high technical quality. Reporting directly to the Chief Technology Officer (CTO), you will be responsible for developing and executing engineering strategies, building and mentoring high-performing leaders and teams, and aligning technical initiatives with business objectives. The ideal candidate will have a proven track record of operating effectively in startup environments at various stages of growth, with a strong focus on building culture and scaling engineering organizations.

What you’ll do:

  • Lead and mentor a distributed engineering team across remote locations in the US and Ukraine.
  • Champion a culture of supportiveness, proactivity, reliability, independence, and efficiency within the engineering organization, promoting skill development and career growth opportunities for team members.
  • Collaborate with product and business counterparts to build roadmaps, advocate for engineering initiatives, and allocate resources optimally for execution.
  • Build and nurture a team of engineering managers (currently 4), including several first-time managers, providing guidance and support in their professional development and leadership journey.
  • Partner with recruiting and engineering leadership to establish a consistent and effective hiring pipeline and process to rapidly scale the team without sacrificing candidate quality.
  • Establish and maintain best practices for software development, including coding standards, architectural design, testing methodologies, and deployment processes to enhance productivity, efficiency, and quality of deliverables.
  • Collaborate with the CTO and other senior leaders to shape the company's technical vision, roadmap, goals, and long-term strategy.

What you’ll need:

  • 5+ years of experience managing managers, building and managing high-performing software teams ideally in a startup environment (fintech and/or b2b a plus)!
  • Excellent leadership and communication skills, with the ability to inspire and motivate teams across distributed locations.
  • Adept at coaching and developing new and repeat managers, fostering a culture of accountability, empowerment, and continuous improvement.
  • Leading teams through varying challenging situations including rapid growth, product pivots, team reductions, strategic partnerships, and team rebuilds.
  • Proficient at setting goals, building roadmaps, and aligning engineering work with short/long-term business objectives.
  • Strong technical background with expertise in modern software development technologies, frameworks, and methodologies.
  • Bachelor's or Master's degree in Computer Science or related field.

Nice to have:

  • Located in Central or East Coast time zones
  • Ability to collaborate with international teams
  • Prior experience managing:
    • Cloud-based architecture
    • SaaS delivery model
    • Payment related activities


This role has an annual starting salary range of $250,000 to $300,000+ equity + benefits. Compensation may exceed this range for exceptional, experienced candidates joining above our posted level.

Benefits & perks that we offer:

  • Unlimited PTO
  • Flexible and remote work culture
  • Competitive compensation and equity
  • Health, dental, and vision coverage for you and your dependents
  • Lunch & commute reimbursement when working in the NYC office located near Union Square
  • $500 home office set up reimbursement
  • $2500 annual growth and development stipend
  • $50 monthly food delivery gift card
  • 401k
  • ERG groups e.g. LGBTQIA+, Women @ Settle, and more!
  • Employee Referral Program
  • Team building events

Our Commitment to You

At Settle we know that cultivating diversity and fostering an inclusive work environment is critical to our impact and success. We create an environment where no individual is advantaged or disadvantaged because of their background. We offer equal opportunity employment regardless of race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability status, age, marital status, or protected veteran status.

With a commitment to maintaining a bias-free environment in which harassment is prohibited, we respect cultural diversity and comply with the laws of the places in which we operate. We expect our business partners, suppliers, clients, and all of our team members to uphold these commitments.