Director of Engineering - TeamUp
DaySmart Software
About Us:
DaySmart supercharges experience-based businesses with innovative, industry-specific software services that power customer and revenue growth. With thousands of partners worldwide and dozens of industry awards, we provide best-in-class solutions to accelerate their business. TeamUp, a DaySmart product, is the most recommended management software for in-person and online classes at fitness studios, boxes, and gyms worldwide.
Position:
We're at an inflection point. We’ve built something special—reliable software that powers over 8,000 fitness businesses that is growing rapidly—but we need the right leader to support the team through the next phase of growth. This is a player/coach role for someone who leads by example, combining hands-on technical contribution with proven people leadership. You'll spend your time building the engineering culture that will scale us through our next phase of growth, making architectural decisions, and writing code alongside your team. This role will report to SVP Technology.
Key Responsibilities:
- Define and lead the engineering vision and strategy, ensuring alignment with overarching business objectives and product roadmaps to drive sustained growth.
- Own the end-to-end development of new products, demonstrating deep technical expertise and a proven track record of building innovative solutions from the ground up.
- Build and scale a high-performing engineering team through strategic hiring, mentorship, and leadership development.
- Demonstrate strong technical leadership with hands-on involvement when necessary, bringing real technical expertise to guide complex engineering challenges.
- Thrive in a fast-paced environment, operating independently, running at speed to meet aggressive timelines, and delivering results without heavy oversight.
- Adopt a go-getter mindset, proactively identifying opportunities, solving problems, and driving engineering initiatives with determination and accountability.
- Establish and enforce engineering best practices to deliver robust, reliable, secure, and scalable solutions that meet evolving business needs.
- Cultivate a culture of innovation, collaboration, and continuous improvement by empowering engineering and product teams to experiment, learn, and deliver impact-driven solutions.
- Drive critical architectural decisions that support long-term scalability, maintainability, and security, ensuring the technology stack evolves alongside business demands.
- Champion agile methodologies by refining sprint planning, execution, and delivery processes to optimize velocity and cross-functional collaboration.
- Streamline CI/CD pipelines and DevOps practices to accelerate release cycles, ensuring rapid, reliable, and high-quality software delivery.
- Manage engineering budgets, resources, and tools with a focus on maximizing operational efficiency, innovation, and return on investment.
Technical Challenges:
- Scale systems handling millions of bookings monthly while maintaining 99.9% uptime
- Modernize architecture without disrupting live customer operations
- Optimize payment processing systems that move real money during peak booking periods
- Improve API performance as customer base grows 50% year-over-year
- Build observability so we prevent issues before customers notice them
- Lead adoption of AI-enhanced development practices using LLMs, agents, and GenAI tooling to accelerate team productivity and code quality
People Challenges:
- Lead engineers through complex technical decisions while developing their judgment
- Balance feature velocity with technical excellence and system reliability
- Establish on-call practices that maintain reliability without causing burnout
- Create documentation and processes that enable rapid team scaling
- Actively coaching team members to find their growth areas and complete their goals
Required Qualifications
Technical Foundation
- 7+ years in software engineering with deep SaaS experience in Python and Django expertise
- 5+ years managing engineering teams, preferably in growth-stage companies
- Strong experience with SQL, database optimization, and performance tuning
- Hands-on experience with AWS services, containerization (Docker), and Kubernetes
- Solid understanding of API design, system scalability, and microservices architecture
- Experience with task queues (Celery), asynchronous programming, and background processing
- Track record of building and scaling systems that handle high transaction volumes
Leadership & Business Acumen
- Experience hiring, developing, and retaining high-performing engineers
- Proven ability to establish team processes and engineering practices that improve outcomes
- Strong communication skills with ability to influence technical and business decisions
- Experience in B2B SaaS environments, ideally with customer-facing systems
- Understanding of agile development practices and team facilitation
Preferred Experience
- Early-stage startup experience
- Multi-product SMB environment
- Payment processing systems and PCI compliance requirements
- Team Topologies concepts and modern engineering organization structures
- Experience with incident response, postmortems, and reliability engineering
- Background in fitness, wellness, or service-based industry software
Salary
- The salary for this role is $200,000 per year. Pay is based on several factors including but not limited to education, work experience, certifications, internal equity, etc.
What We Offer
- Comprehensive benefits package including medical, dental, and vision insurance.
- 401(k) plan with company match.
- Open PTO and a generous paid holiday schedule.
- Supportive work environment with the flexibility to work where/how you want – in-office, remote, or hybrid.
- Flexible work arrangements, including remote work options.
- Opportunities for professional development and career growth.
How You Will Work
This is a 100% remote position within the United States. We offer flexible work arrangements including fully remote, in-person, or hybrid opportunities. For those looking to work in person, we have physical offices in the following cities:
- Ann Arbor, MI
- Scottsdale, AZ
- Wayne, PA
- Austin, TX
Many DaySmart employees primarily work from home, and our teams are structured to operate efficiently in a distributed environment. While we don’t always share a physical office, we work together closely through remote collaboration practices.
We maintain a highly collaborative culture and expect all employees to actively participate in meetings, discussions, and team interactions. This includes joining scheduled video calls with cameras on, contributing to conversations, and being fully present.
We believe that strong communication and visual connection are essential to maintaining alignment, accountability, and trust across our teams. At DaySmart, working remotely comes with the responsibility to show up, engage, and collaborate with intention.
Your safety is important to us!
We’ve recently identified an increase in fraudulent activity targeting individuals who have applied to positions at DaySmart. Please note that any legitimate communication regarding your application will come either from an official DaySmart email address (ending in @daysmart.com) or directly through our Applicant Tracking System.
Please refer to DaySmart Privacy Policy to learn more about how we are committed to respecting your privacy and the security of your personal information.
DaySmart is committed to creating a diverse employee environment and is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, sexual orientation, national origin, disability, age, or veteran status.