For 25 years, DrFirst has empowered providers and patients to achieve better health through intelligent medication management. We improve healthcare workflows and help patients start and stay on therapy with end to end solutions enhancing prescription access, affordability, and adherence. Our solutions help 100 million patients a year and are used by more than 420,000 prescribers, 71,000 pharmacies, 270 EHRs and health information systems, and over 2,000 hospitals in the U.S. This is a great opportunity to be a part of a successful Healthcare IT company experiencing significant growth. Here you will get to work with some of the smartest and most interesting people around, solving unique and complex challenges in healthcare on a scale matched by few companies. If you get excited about stretching yourself in new ways, developing yourself to your fullest potential, and care about working with smart colleagues, we want to talk to you.

The Director, Support Delivery is a senior technical leader responsible for escalation and triage excellence, and for building the next generation of expert technical support specialists at DrFirst. This is not a role about running day-to-day support operations — it is a role about technical depth. The Director owns how the hardest cases are diagnosed, how escalations are reasoned through, and how that expertise is transferred to the people who deliver support every day. 

Reporting to the VP, Customer Operations, the Director works embedded within the Product organization, serving as the technical bridge between support and engineering. The core measure of success is twofold: the rigor and speed with which complex issues are triaged and escalated, and the demonstrable growth in technical capability of the specialists the Director develops. 

We are looking for a diagnostician and a teacher — someone who approaches a difficult case the way a physician approaches a differential diagnosis, working from symptoms to the full range of possible causes before landing on resolution, and who can teach that same reasoning to others. This is a deeply technical leadership role: the mandate is the craft of complex resolution and the development of technical talent, not the day-to-day management of support operations. 

The role includes an immersive ramp — time embedded with our Product organization and hands-on with our support practice — designed to build the product fluency and floor credibility this Director leads from before taking on the senior technical specialists they will develop. 

Escalation & Triage Leadership 

• Own the technical triage and escalation discipline for the support organization — how complex cases are diagnosed, reasoned through, and routed to resolution 

• Build and maintain the escalation framework: triage criteria, handling standards, resolution ownership, and clear definition of what constitutes a product escalation versus a support execution issue 

• Serve as the senior technical decision-maker on the most complex and highest-impact escalations across partner and enterprise accounts 

• Ensure escalation decisions are made at the right level and that difficult cases reach senior technical intervention when they should 

Building Technical Experts 

• Develop a bench of expert technical support specialists — the primary measure of success in this role 

• Teach diagnostic and triage reasoning as a transferable skill, not just resolve cases personally 

• Define and raise the technical competency standard across the specialist capability ladder 

• Directly lead and mentor the organization’s most senior technical support specialists 

Product Partnership 

• Work embedded within the Product organization as the primary technical interface between support and engineering 

• Build a systematic feedback loop between support escalation trends and the product roadmap — ensuring support signal informs prioritization rather than reactive bug reporting 

• Track escalation patterns by product, workflow, and customer segment to identify recurring failure points and advocate for resolution at the product level 

• 7+ years of progressive experience in technical support, with significant depth in complex technical troubleshooting and escalation handling in a SaaS or healthcare technology environment 

• Demonstrated diagnostic and triage capability — a structured, hypothesis-driven approach to isolating the cause of complex technical issues 

• Proven track record of developing technical talent and raising the capability of a team through direct mentorship and defined competency standards 

• Experience designing or owning escalation frameworks — building the structure through which escalations are handled, not just managing them 

• Direct experience partnering with Product or Engineering teams on escalation feedback loops and product-informed resolution 

• Comfort operating in a technical, hands-on capacity and a willingness to complete a hands-on product and onboarding ramp before leading the team 

• Experience in an AI-enabled support environment a plus 

• Bachelor’s degree required; advanced degree in a technical, business, or related field a plus 

If you are a technical diagnostician who loves solving the hardest problems and takes genuine satisfaction in making the people around you better — we want to hear from you. This is a high-impact role with direct visibility to executive leadership and meaningful influence over how DrFirst serves its customers every day. 

• 90% Desk, phone, and virtual meeting work.
• 10% Travel to client sites, conferences, or internal team meetings.

#LI-GF1  #LI-Remote

• Competitive compensation, with a base salary of $135,000 to $158,000 (Exact compensation may vary based on skills and experience) 
• Eligible for Company Performance based Bonus Program, based on individual and company performance
• Medical, dental, and vision insurance
• 401K eligible after 3 months of employment, with 50% company match up to first 5% of salary contributed to the plan with a 3 year vesting schedule
• HSA for eligible employees enrolled in the HDHP, with a generous company contribution up to $500 for individual coverage and $1000 for family coverage per year
• 100% company paid short and long term disability, AD&D, and group life insurance
• Accrued annual paid time off (PTO) of 18 days for the first 3 years of service, increasing thereafter and 7 paid holiday days
• Employee Assistance Program
• Continuing Education funds up to $1500 annually for eligible programs after 1 year of service
• Voluntary benefits including FSA, Hospital indemnity, Accident and Critical Illness insurances

DrFirst is committed to being a Remote First company, creating a dynamic and flexible workplace where everyone thrives, no matter where they log in from. Check out our approach to remote work at https://drfirst.com/company/about-us/careers/.

Our recruitment process at DrFirst is straightforward and secure. You will only be contacted by our recruitment team through an official @drfirst.com email address. We will never ask you for payment or sensitive personal information, such as your social security number or banking details, at any stage of the hiring process. Additionally, we will not request that you purchase equipment or accept e checks or checks for deposit. If you encounter any communications claiming to be from DrFirst that seem suspicious, please contact our recruitment team directly at recruiter@drfirst.com to verify the message authenticity. Your security is important to us.

Learn more about our benefits and professional development opportunities at https://drfirst.com/company/about-us/careers/the-perks/.