Head Of Engineering


About us

CollegePlannerPro is the market-leading end-to-end practice management software for independent college consultants. Our robust B2B SaaS platform provides counselors with a multitude of tools for operating an independent business practice and providing expert college admissions guidance. Our top priorities are to listen to, understand, and swiftly support the needs of our members.

We are a completely remote team of 6 full-time individuals, with the majority of our team and clientele based in the United States. We are self-funded, profitable, and have been proudly serving the independent educational consultant (IEC) community since 2009. We believe in the ability of our small but mighty team to maximize the potential of our members’ businesses and students through the technology we create. We value colleagues who are resourceful, communicative, respectful, and operate with pride, not ego.


As the most senior level technology-focused employee at CollegePlannerPro, the Head of Engineering will be in charge of all company technology and technological resources. They will establish technology vision and strategies. They should have a passion for coding, managing a small team, and bringing industry best practices to the group.

The Head of Engineering will report directly to CEO Valerie Kaskovich. They will be responsible for architecture, development, quality assurance, and maintenance on our existing platform, as well as management of two mid-level developers. We will entrust the Head of Engineering with significant autonomy to guide the technical direction of our products. We prioritize optimizing the reliability, maintainability, and usability of code written and the systems designed in order to deliver the best possible experience for our members and their students. As a result, we encourage our technical teammates to be product-minded and take great care in allowing our technology to thrive in both the near- and long-term.

The Head of Engineering role

We’re looking for a talented new teammate who is enthusiastic about and experienced with a fully-remote position. Physical location is very flexible, but in order to be most effective we are seeking a Head of Engineering whose schedule is flexible enough to overlap with employees based in Pacific Time for at least half of a normal workday (~9am-5pm).

Employment classification: This is a full-time position (W2 employment). Candidates must be authorized to work in the United States in order to qualify for this position (no sponsorship).

The Head of Engineering is a multifaceted role, both people-focused and highly technical. Responsibilities will include:

  • Leadership: Align stakeholders’ interest with technical vision, lead the company’s technical architecture, document decisions, mentor developers.
  • Technical: Assist with the migration of our codebase to the latest technology, fix and improve our code quality and performance, apply programming and security best practices, basic DevOps / CI-CD, manage a production AWS account, maintain and improve SDLC processes, scope out projects, advise on technical implementation.
  • Management: Work closely with the product team to align the project management goals with the company’s goals, oversee the technical sprint cycle (creating requirements, assigning tasks, reviewing code, tracking progress, etc).

Desired qualifications

We’re looking for a Head of Engineering who is deeply passionate about technology and happy to wear many hats. The requirements and qualifications include:

Non-Technical Qualifications

  • Traits: Big picture thinker, willing to work with a variety of stakeholders, excellent verbal and written communication skills, conscientious, ability to project / estimate timeframes and deadlines, fast learner, resourceful, multi-tasker
  • Experience: Managed a small team of developers, worked within an Agile/SCRUM framework, start-up experience, worn multiple hats, can prioritize work within a dynamic environment, production level bug handling / debugging experience
Technical Qualifications

  • Length of Experience: 8-10+ years in software development, 5+ years in a high traffic web environment, 3+ years in a management or leadership role
  • Desired Experience: Legacy code refactoring, Bash/python scripting, Automation workflows, PHP5 to PHP7 migration, Code quality improvements (Big O, N+1, DRY issues…), NextJS, Nginx, Advanced MySQL (DB design, schema migrations, multi-tenant databases, database tuning, normalization, InnoDB vs MyISAM…), Performance monitoring and improvement, Web security experience, Automated testing, SMS / Email transactional processing (Twilio + SendGrid preferred), Payments gateway API integration (BrainTree preferred), Data migration experience, Managing production Linux servers, Familiarity with networking, Basic IT management skills, Website monitoring and alerting, Load testing
  • Required skills: PHP5, PHP7, MySQL, Redis, JavaScript, ReactJS, Node.JS, Bash/Linux, Docker, AWS (ECS, S3, ELB, VPC), Linux
  • Preferred skills: REST APIs, TypeScript, GraphQL, OAuth 2.0 + OpenID, Laravel, Redis-based Queues, Python/Celery, ElasticSearch, Sentry Transactions
  • Desired Tools: Postman, Git, TravisCI, Jenkins, OpenVPN, JIRA + Confluence, Selenium / Ghost Inspector, Slack, OpsGenie / PagerDuty, CloudFlare

Diversity & inclusion

We’re committed to building a diverse team, and all qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. At our core we believe deeply in diversity, inclusiveness, and acceptance as all being key parts of a healthy team.

Compensation & benefits

  • Salary + potential bonus
  • Fully remote role and team (flexible hours and location)
  • Flexible PTO
  • Medical, dental and vision insurance options
  • 401(K)
  • Paid Family Leave


Please submit your resume along with a brief note explaining your interest and providing links to any relevant projects you have spearheaded. If selected, the next step will be a brief (20 minute) self-recorded video interview at your convenience (you may also complete this audio-only with camera covered).

The subsequent round in the interview process involves a brief series of technical challenges and, if passing, a Zoom "code review" to discuss your solutions with a member of our technical team. Applicants who advance will have a final Zoom interview with management.

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