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The Human Resources Senior Director will lead HR policies and programs, develop talent strategies, ensure legal compliance, and mentor HR team members.
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You have seen what happens when HR operates purely in reactive mode. Tickets get closed, forms get filed, fires get put out. But nobody is asking the harder questions: Are we paying people fairly? Are our systems actually connected? Is this manager situation a one-time thing or a pattern? Does leadership even know what they do not know about their people?
SureCost does not want that version of HR anymore.
SureCost is a PE-backed healthcare technology company that helps pharmacies purchase smarter, stay compliant, and work more efficiently. With approximately 65 employees and a fully remote team, we are at a stage where the business is growing and HR needs to grow with it. We have the foundation: an HRIS, core policies, and an experienced team. What we are missing is the strategic layer. Someone who looks at what exists, sees what is fragmented or underbuilt, and knows exactly how to close the gap.
This role reports directly to the CEO and has the full scope of HR: systems, recruiting, compensation, performance, employee relations, and culture. You will be the only HR professional at the company, which means you own all of it. The tactical and the strategic. The day-to-day and the long game. If you are energized by that kind of ownership rather than overwhelmed by it, we should talk.
This is NOT the right role if you...
WHEN YOU ARE CONSIDERING A NEW ROLE, YOU HAVE QUESTIONS. HERE ARE THE ONES WE HEAR MOST.What is the current state of HR at SureCost?
Functional but fragmented. There is an HRIS, a handbook, and established policies. But some tools and processes have grown up separately rather than as part of a cohesive system. The person in this role before stepped down after doing solid foundational work in a more tactical capacity. The opportunity now is for someone to take a clear-eyed look at what is in place, identify what needs to be connected or rebuilt, and bring a level of strategic thinking to the function that has not existed here yet.
What does a typical week look like in this role?
It will vary, especially early on. In the first few months, expect a lot of discovery: auditing systems, getting to know the team, sitting with the CEO to understand the business priorities and where HR can make the most impact. Beyond that, a given week might include a recruiting debrief, a compensation benchmarking exercise, a one-on-one with a manager navigating a people issue, and a presentation to leadership on a policy update. There is no typical week. There is a clear mission and your judgment about how to execute it.
What does success look like in year one?
A consolidated, streamlined HR tech stack with less duplication and more visibility. A compensation philosophy that is documented, defensible, and understood by managers. A recruiting process that is structured and consistent. And a CEO who feels like HR is a function they can rely on strategically, not just a service desk. The bigger goal is that by the end of year one, the HR function reflects the ambition of the business, not just where the business has been.
What is the culture like at SureCost?
Collaborative, low-ego, and mission-driven. The team genuinely cares about the pharmacies they serve and about each other. Because the company is PE-backed, there is real growth ambition and a bias toward getting things done. Remote-first means the culture lives in communication habits, team rituals, and how people show up for each other without being in the same room. The person who thrives here is someone who builds trust quickly, communicates proactively, and does not need to be the loudest person in the meeting to have influence.
What are the benefits like?
Competitive health, dental, and vision coverage. 401(k) with company contribution. Annual bonus eligibility. Flexible time off and company holidays. And a direct reporting relationship to the CEO that gives you real visibility into where the business is going and a genuine seat at the table for how it gets there.
HOW TO APPLY — PLEASE READ THIS CAREFULLY
We are not looking for a polished resume that checks every box. We are looking for someone who has done this kind of work, knows what it actually takes, and can articulate that clearly.
Step 1: Submit your application online.
Start by completing the online application, where you will upload your resume. You can find the posting and apply directly at surecost.com/careers.
Step 2: Send us a cover letter that actually tells us something.
In addition to your online application, please email your cover letter (one page maximum, no templates) to [email protected]. We want to hear you answer the following two questions in your own words:
Your online application gets you in the system. Your cover letter is what gets you noticed. Cover letters that read like they were written to match a job description will not move forward. Cover letters that read like they were written by someone who has actually done this work will.
SureCost is an equal opportunity employer.
We are committed to building an inclusive environment where people of all backgrounds can do the best work of their careers.
SureCost does not want that version of HR anymore.
SureCost is a PE-backed healthcare technology company that helps pharmacies purchase smarter, stay compliant, and work more efficiently. With approximately 65 employees and a fully remote team, we are at a stage where the business is growing and HR needs to grow with it. We have the foundation: an HRIS, core policies, and an experienced team. What we are missing is the strategic layer. Someone who looks at what exists, sees what is fragmented or underbuilt, and knows exactly how to close the gap.
This role reports directly to the CEO and has the full scope of HR: systems, recruiting, compensation, performance, employee relations, and culture. You will be the only HR professional at the company, which means you own all of it. The tactical and the strategic. The day-to-day and the long game. If you are energized by that kind of ownership rather than overwhelmed by it, we should talk.
This is NOT the right role if you...
- Expect to hand off administrative work to a coordinator or assistant
- Need a fully mature, well-documented HR function to be effective
- Are more comfortable maintaining systems than assessing and improving them
- Have spent most of your career in large HR departments with narrow specialization
- Want a role where strategic priorities are handed down to you rather than shaped by you
WHEN YOU ARE CONSIDERING A NEW ROLE, YOU HAVE QUESTIONS. HERE ARE THE ONES WE HEAR MOST.What is the current state of HR at SureCost?
Functional but fragmented. There is an HRIS, a handbook, and established policies. But some tools and processes have grown up separately rather than as part of a cohesive system. The person in this role before stepped down after doing solid foundational work in a more tactical capacity. The opportunity now is for someone to take a clear-eyed look at what is in place, identify what needs to be connected or rebuilt, and bring a level of strategic thinking to the function that has not existed here yet.
What does a typical week look like in this role?
It will vary, especially early on. In the first few months, expect a lot of discovery: auditing systems, getting to know the team, sitting with the CEO to understand the business priorities and where HR can make the most impact. Beyond that, a given week might include a recruiting debrief, a compensation benchmarking exercise, a one-on-one with a manager navigating a people issue, and a presentation to leadership on a policy update. There is no typical week. There is a clear mission and your judgment about how to execute it.
What does success look like in year one?
A consolidated, streamlined HR tech stack with less duplication and more visibility. A compensation philosophy that is documented, defensible, and understood by managers. A recruiting process that is structured and consistent. And a CEO who feels like HR is a function they can rely on strategically, not just a service desk. The bigger goal is that by the end of year one, the HR function reflects the ambition of the business, not just where the business has been.
What is the culture like at SureCost?
Collaborative, low-ego, and mission-driven. The team genuinely cares about the pharmacies they serve and about each other. Because the company is PE-backed, there is real growth ambition and a bias toward getting things done. Remote-first means the culture lives in communication habits, team rituals, and how people show up for each other without being in the same room. The person who thrives here is someone who builds trust quickly, communicates proactively, and does not need to be the loudest person in the meeting to have influence.
What are the benefits like?
Competitive health, dental, and vision coverage. 401(k) with company contribution. Annual bonus eligibility. Flexible time off and company holidays. And a direct reporting relationship to the CEO that gives you real visibility into where the business is going and a genuine seat at the table for how it gets there.
HOW TO APPLY — PLEASE READ THIS CAREFULLY
We are not looking for a polished resume that checks every box. We are looking for someone who has done this kind of work, knows what it actually takes, and can articulate that clearly.
Step 1: Submit your application online.
Start by completing the online application, where you will upload your resume. You can find the posting and apply directly at surecost.com/careers.
Step 2: Send us a cover letter that actually tells us something.
In addition to your online application, please email your cover letter (one page maximum, no templates) to [email protected]. We want to hear you answer the following two questions in your own words:
- Describe a time you stepped into an HR function that was working but underperforming. What did you find, what did you prioritize, and what changed because of your work?
- What is the most common mistake HR professionals make when they inherit a function from someone who was strong tactically but limited strategically?
Your online application gets you in the system. Your cover letter is what gets you noticed. Cover letters that read like they were written to match a job description will not move forward. Cover letters that read like they were written by someone who has actually done this work will.
SureCost is an equal opportunity employer.
We are committed to building an inclusive environment where people of all backgrounds can do the best work of their careers.
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