Chief Technology Officer


Chicago, IL, United States

Toronto, Ontario, Canada

Position Details

Parking is quite intriguing given that the future of the industry is being defined right in front of us. As we continue to monitor new trends, we’re still focused on trying to solve a real problem and that’s to help businesses and consumers find off-street parking with ease. Present in over 8000 locations, airports, and venues such as Madison Square Garden, Fenway Park, Wrigley Field, SpotHero is changing the way drivers park daily. We solve parking and we have market fit. It's a simple problem with such complex solutions and we’re always looking for ways we can add value such as partnership with Lyft, our SpotHero IQ product, CarPlay & Android Auto integrations, and more. This year, SpotHero hit $1B GMV, parked 50M+ cars to date, and continuing the focus on understanding our drivers to provide the best experience possible.

As the leader in this space, SpotHero connects drivers to 8,000+ parking locations across 300+ cities. We have an incredible board, including Sam Yagan, former CEO of Match Group. We’ve partnered with Apple, Google, Lyft, and Waze to bring best-in-class parking to as many North American drivers as possible.

SpotHero is seeking a Chief Technology Officer who will serve as a key member of our executive team, collaborating closely with senior leadership to drive company strategy. You will have the exciting opportunity to navigate, lead, and scale the Engineering department and company to support our hyper-growth company. 

CTO Role and Responsibilities:

As CTO, you will be a strong operational business partner, managing the technology infrastructure across the company and leading an engineering organization that leverages process excellence and automation as we continue to scale. You will have strong technical planning capabilities and bring a strategic and well defined vision to evaluating technical architecture, system management, and continuing the development and growth of our current engineers and managers. You will oversee and build a world class team and have a meaningful and measurable impact across the company.

  • Collaborate with Engineering Leadership to build a technology vision and empower leaders to create strategies for technology platforms, partnerships and external relationships.
  • Deliver a strategic roadmap while collaborating with Product in helping manage trade-offs and compromises between engineering and Product to balance new development, sales support, and technical debt.
  • Excel at producing a strategic roadmap that moves the needle on Quality, Automation and Business Continuity.
  • Create and foster an environment conducive to innovation, high productivity, and high quality.  
  • Track engineering quality and throughput using empirical data and methodologies.
  • Drive a software development lifecycle process and culture that ensures the appropriate balance in which quality products are produced in a fast-paced, dynamic environment.
  • Empowers leaders to own, identify, compare, select, and implement technology solutions to meet current and future needs.
  • Create a strong internal culture to manage technology projects with accurate time estimates, adherence to deadlines, and strong communication to stakeholders.
  • Track, analyze and monitor technology performance metrics.
  • Take the initiative in thought leadership, innovation, and creativity.


  • 10+ years experience leading in a high-growth or start-up organization, with 5+ years in SVP, CTO, CIO, CSIO, CXO leadership role.
  • Ability to navigate evaluating technical designs against business impact in a data-driven manner.
  • Strong familiarity with distributed systems as it relates to balancing tech debt, quality, and business impact. 
  • Must be able to work in a dynamic, rapidly changing environment and interact with partners and stakeholders directly.  
  • Exceptionally self-motivated and directed, with top-notch interpersonal and communication skills.  
  • Directly responsible in building an engineering team of at least 100 individuals.
  • Proven track record in advancing technology roadmap or capabilities.
  • Bachelor's degree or equivalent technical certifications in relevant technologies.
  • Superior presentation skills and engaging presence to help influence different constituencies and business leaders with varying degrees of financial and technical acumen.

Personal Characteristics: 

You are intellectually curious, operationally-oriented, and highly collaborative. You handle stressful situations in a professional and balanced manner and will serve as a mentor, leader, and partner across the organization in a dynamic environment. Always willing to roll up your sleeves with an attention to excellence at all levels, you will be a leader when it comes to doing the work and leading the team. 

  • Understands what makes up the current engineering environment and provides a clear vision for the team that is connected to addressing key problems while inspiring everyone to participate meaningfully.
  • In tune with the business operations and how Engineering can help evolve/grow where the business is going to yield various ROI outcomes.
  • Highly open minded and is accepting of meaningful suggestions and insights to help the operating units make the most effective decisions.
  • Not afraid to speak your mind and challenge common thought processes.

Critical Leadership Capabilities:

Strategic Mindset

  • Possesses intellectual curiosity and rigor that can contribute to identifying areas of future opportunity as the company continues to evolve as the leader in the parking industry.
  • Ability to effortlessly translate the broad strategies of SpotHero into clear, specific objectives and plans for units and individuals.
  • Looks outward as well as 2-3 years onward.

Operational Leadership

  • Enables higher performance by furthering the technical capabilities and insights of the Engineering function and by contributing to operational issues for senior leadership and the Board.
  • Knits the Engineering function into the larger business to drive growth and innovation for SpotHero.
  • Identifies new processes, procedures, and systems to improve productivity and to make SpotHero more efficient.

Team Leadership

  • Communicates long-term direction and collaborates with team on how to reach it though open, inquisitive, and constant learning.
  • Directs the strategic objectives of SpotHero to the whole team with clear and explicit intent; fostering an enthusiasm for excellence.
  • Fosters and embodies transparent communication, encouraging self-awareness and leading the team by complementing its strengths and weaknesses. 
  • Holds team members accountable for their commitments, while also encouraging them to take risks and to try new things to continuously drive growth.  

Emotional Intelligence

  • Highly personable and relationship-driven. Mature and insightful.
  • Capable of commanding the respect of colleagues as well as the Executive Board, stakeholders, and other external counter-parties. A strong, effective communicator who can tell any story clearly.

Technology we use:

  • Our Back End Stack is: Monolith using Django/Python/PostgreSQL. We are moving our Monolith to a Modular Monolith, using Domain Driven Design. When relevant we extract specific domains to Services currently using Java, Kotlin and GoLang. We also use Docker, deploy our apps via Kubernetes. We use Kafka for asynchronous-, and gRPC for synchronous service-to-service communication. 
  • Our Front End Stack is: Our Front End stack is React/Redux, Sass, Jest/React Testing Library/Cypress, and Webpack. We maintain a private npm repository with shareable UI components, utility functions, Babel/ESLint/Prettier configurations, and custom tasks.
  • Our Data Stack is: Our Monolith Database is Postgres and Redis for caching. We also use Redshift as our data warehouse and S3 as our data lake. The data lake is queried using Presto. We use Airflow and Spark for ETL, as well as do some stream processing (Kafka Streams and Spark at the moment). Our Model pipeline uses scikit-learn, pandas. Our analysts utilize Looker as our Business Intelligence tool. And we use Quicksight for Dashboard on our external Data Products.
  • Our Dev Tools Stack is: AWS+Kubernetes for hosting. Terraform + Helm Charts for IaaS/Deployment. ConcourseCI for CI/CD. Prometheus/Alertmanager/VictorOps for team alerting. We’re starting to work on multi-region available services.

What We Are Offering:

  • Career game changer – A truly unique experience to work for a fast growing startup in a role with unlimited potential for growth.
  • Excellent benefits – We cover 90% of Medical Premiums, 50% of Dental & Vision Premiums, and offer company sponsored Life Insurance.
  • Flexible PTO policy, generous parental leave, and great work/life balance – We value and support each individual team member.
  • Fun perks like snacks, catered lunches, happy hours, wellness programs, and SpotHero swag.
  • Annual parking stipend (duh – we help people park!).
  • The opportunity to collaborate with fun, innovative, and passionate people in a casual, yet highly productive atmosphere.
  • A workplace recognized as the Startup of the Year by Built in Chicago, a Top Workplace by Chicago Tribune, and one of Chicago’s Best Places to Work for Women Under 35 by Crain’s Chicago Business.
  • A workplace recognized as a Best Place to Work by Built In Chicago, Top Company Culture by Entrepreneur, and one of TIME’s 50 Genius Companies.
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50M+Cars Parked

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