Director of Technology
Remote Worker - N/A
Job Type

Reporting to the Chief Technology Officer, a PICKUP Director of Technology will be responsible for leading an amazing and talented team of software engineers who are responsible for designing and implementing microservice and API solutions that have scale, speed and are running in both public and private clouds. This role requires the ability to balance between people management, leadership, and technical responsibilities. You will collaborate with senior product, operational, and other business leaders while leading multiple technology teams to create market differentiating products and features on our “Supply” side of the technology stack. This position is an excellent opportunity to drive the future of our software framework and helping drive our high-growth strategy.

Alongside our business values, PICKUP’s technology group strives to demonstrate shared purpose and learning across our organization. We expect this role to lead by example.

The Director of Technology role will also be responsible for mentoring and growing team members within the engineering organization. The Director of Technology will also be a partner in determining the future direction of the engineering organization and being a part of the execution of that direction.


  • Drive a results-oriented team and culture with a strong focus on execution, quality, and speed
  • Work closely with the product management organization to develop and deliver on roadmaps
  • Recognize process and product gaps early and able to drive changes to achieve better outcomes
  • Evangelize the product vision internally and externally and represent the company, product, and team at all levels
  • Strong executive presence and ability to champion ideas and initiatives
  • Be the subject matter expert, mentor, and coach to the engineering team
  • Foster innovation in a collaborative way with the organization to develop new software designs and technical debt solutions
  • Develop architecture and design alternatives with senior engineers and lead cross-departmental projects 

  • 10+ years’ experience in Software Development
  • 3+ years’ managing a team
  • BS in Engineering or related degree (or equivalent work experience)
  • 8+ years’ experience using C# /.NET standards and patterns
  • 3+ years’ experience with public clouds (AWS/Azure/GCP)
  • Solid experience writing unit and integration tests
  • Experience with HTML/CSS/JS (Angular/React a plus)
  • Experience with distributed/event-based architecture
  • Experience with microservice/serverless architecture
  • Expert knowledge of Agile design methodologies; experience creating design documentation, roadmaps, and coding standards
  • Experience with Kubernetes a plus
  • Experience with high performance network and security platforms
  • Knowledge of the hosting industry a plus
  • Knowledge of cloud lifecycle deployment and automation frameworks 


  • Excellent ability to communicate effectively with others using spoken and written English including the ability to communicate with technical and non-technical stakeholders.
  • Ability to resolve technical issues with versatility, flexibility, and proactive thought
  • Excellent planning skills, including the ability to organize, prioritize and control job responsibilities in order to meet deadlines in an environment with overlapping and potentially conflicting priorities
  • Expert analytical, troubleshooting and problem-solving abilities
  • Ability to expertly solve complex technical problems
  • Expert knowledge of non-functional requirements including security, scalability, and usability
  • Expert knowledge of software design patterns, principles, and practices
  • Demonstrated ability to develop and support a scalable API platform 
  • Keen attention to detail