Head of Product Management

Head of Product Management

We're seeking a dynamic individual with a deep understanding of product development, a systems-thinking mindset, and a strong engineering background. This person should possess an entrepreneurial spirit, a passion for data analysis, and the drive to influence key metrics that will propel the organization forward. If you're excited about making a significant impact through innovative product strategies and complex problem-solving, we'd love to have you on our team!

About the team you’ll join

We’re a team of driven, conscientious individuals with a clear mission: to make accounting and payroll fast, simple, and affordable for millions of American businesses and their accountants. 

It’s not enough to have a “good job”. It takes connection, culture, encouragement, growth opportunities, challenges, communication, and so much more to create an environment where people and ideas flourish. 

We are Patriot Software; a hybrid remote company with 175+ employees across the United States and a co-working space in Canton, Ohio. 

Our search for a new team member always starts by seeking a quality individual who desires to live by our core values:

1. Be Customer Obsessed - In everything we do, we start with the customer and work our way backwards. Our primary focus is how we deliver tremendous value for the American businesses we serve.
2. Lead With Speed - We believe in doing things quickly and not being afraid to take big chances. Moving fast and making bold moves is how we stay ahead.
3. Don’t Cut Corners - We don’t skimp on quality. We make sure to own our technologies, development, and operations so that the entire experience is the best it can be.
4. Create a Better Us - We’re always improving by keeping it simple, saying no to things that don’t help our customers, automating what we can, and spending our money wisely.
5. Follow The Golden Rule - We treat others how we would want to be treated, disagree and commit, and welcome feedback from anyone, anywhere in the company.
6. Grow, Be a Leader - We look for leaders at all levels and always put the customer and team above ourselves. We want to build a pro team of high-caliber players, with high accountability and trust across all individuals.

Interested in learning more? Great! Read on to see if your skills are a match, too.  

What You’ll Be Doing: 

• Own Product Strategy Execution – Shape strategic direction and execute relentlessly. Ensure a seamless, high-quality customer experience.
• Define Great Metrics – Establish meaningful product KPIs that enable us to be inventive and experiment boldly. Talk to customers frequently to surface anecdata. 
• Analyze Market & Competition – Stay ahead of trends, research competitors, and translate insights into product direction.
• Lead & Develop the Team – Hire, coach, and retain top talent. Foster a culture of high performance.
• Collaborate & Influence – Work cross-functionally to drive strategic decisions based on data, insights, and customer needs across Engineering, Design, and the broader organization. 
• Build a Strong Product Culture – Encourage rapid testing, knowledge-sharing, and transparency.

Please note this is a sample of what you’ll be doing. This job requires you to be able to adapt to change quickly in order to deliver an exceptional customer experience. Your duties, responsibilities, and activities may change at any time with or without notice.

Some Examples of Recent Work:

• Own the whole-company internal communications around our product vision and strategy
  The Head of PM took point on crafting the internal communication strategy around our product vision and strategy, and then went out and helped stump across the org to align all departments.
• Roll out product analytics across the company
  The Head of PM led the effort to pick and set up our new product analytics tool. That meant managing the sales process, figuring out technical needs, and working with Engineering and Data to get it running right.
• Run roadmap and feedback meetings with top customers
  The Head of PM takes point on meetings with our biggest customers—sharing what’s coming next and collecting feedback. PMs join in, but the Head of PM drives the prep and keeps it moving.
• Update our roadmap strategy in light of AI
  As AI and LLMs change how businesses work, the Head of PM leads the charge on figuring out what that means for our product—and how we need to adapt.
• Prep board materials and align with the CEO
  The Head of PM helps put together board decks and works with the CEO to share where we’re going, what’s changing, and what risks or opportunities are ahead.
• Spot cross-product risks and opportunities
  The Head of PM regularly reviews customer calls, chats, emails, and churn reasons to find patterns. This helps catch issues or opportunities that might slip through if we only looked at each product in isolation.

What You Bring: 

• 6+ years in product management, including 3+ years in SaaS, with a proven ability to align teams, drive strategy, and execute effectively.
• 5+ years leading teams, scaling product organizations, coaching, and developing high performers.
• Deep technical knowledge—either a background in engineering or a very strong understanding of software development.
• Data-driven mindset—define, track, and leverage key metrics to guide decisions.
• Strong leadership in competitive analysis, driving processes to identify and research competitors, and maintaining up-to-date market intelligence.
• Experience collaborating with key stakeholders to understand their needs, leverage data, and identify new opportunities.
• Excellent communication and collaboration skills—you should be one of the best writers you know (concise, clear, and plainspoken).
• Proven ability to foster a strong product culture through rapid testing, knowledge-sharing, and breaking down silos.
• Entrepreneurial and gritty—comfortable with ambiguity, problem-solving, and taking ownership.
• Commitment to high-quality UX—deep understanding of user flows, interfaces, and product design.
• Strong understanding of high-quality products, with the ability to assess and communicate visual design, user interfaces, user flows, and overall user experience to ensure an intuitive and engaging product.
• Deep knowledge of modern discovery and test validation methods, with a proven track record of building trust and being a reliable partner to stakeholders and business leaders.
• Consistent, reliable high-speed internet access
• Dedicated, quiet workspace free from distractions

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

Location & Commitments:

Full-time, Direct Hire and 100% Remote role

This position is open to all candidates who legally reside and are eligible to work in the United States. This position is currently not open to applicants in the following locations: Alaska, California, Hawaii, Washington D.C.

Working hours are established by each team and department based on business needs.  For this role, core working hours are typically between 9am - 5pm EST, Monday through Friday, but we’re flexible. Due to the nature of our businesses, we have busy seasons and “right-nows” that occasionally require working outside of core hours.

Patriot is an equal opportunity employer. We do not discriminate against any employee or job applicant on the basis of race, color, gender, national origin, age, religion, creed, disability or sex.

More Reasons to Love Patriot:

We pride ourselves on our company culture and value our employees’ hard work. Aside from the freedom to introduce new ideas or technologies, here are some of the awesome benefits our full-time employees enjoy:

• Remote-first work
• Paid time off and paid holidays
• Medical, dental, and vision insurance 
• Section 125 HSA and FSA accounts
• Benefits starting 1st of the month after hire
• Company-paid life, short-term, and long-term disability insurance
• 401(k) with company match
• Up-to-date hardware and equipment provided
• Flexible scheduling and opportunities for advancement
• Engaging and collaborative company culture
• Education reimbursement 

Are you ready to take the next step in your career?

This position has a starting salary of $160K - $190K

Note, respecting the privacy of our customers & employees is an essential part of our privacy program. Please do not submit the following Personally Identifiable Information (PII) such as Social Security Number, Date of Birth, W-2's, etc. with your application.

Thank you for your interest in Patriot Software! As part of our commitment to a fair and efficient hiring process, we use AI-powered tools to assist with note-taking, resume screening, and interview insights. These tools help us evaluate candidates consistently while ensuring compliance with EEOC (Equal Employment Opportunity Commission) guidelines and other applicable laws.

Our AI tools do not make final hiring decisions—all decisions are made by our hiring team. We remain committed to equal opportunity hiring, and all applicants are evaluated based on qualifications, skills, and experience.

By submitting your application, you acknowledge and agree to the following:

• AI Usage
• AI may be used to analyze and/or collect data from the applicant's video, including facial expressions, and to consider their fitness for a position.
• AI programs may be used in our interview process (i.e. notetaking, evaluating responses, interview synopsis, etc). 
• On-Camera Video Interviews:
• I understand as a part of Patriot’s hiring process all interviews will be conducted via video with cameras on to maintain compliance and security standards.
• Additionally, as a company, Patriot defaults to cameras-on for all video interactions. 
• Photo Capture for Security Purposes:
• If I am selected to interview, I may be asked to provide or have a photo captured during the process.
• I understand that this photo will only be used to verify that the same candidate is present throughout all stages of the interview process.
• Privacy and Data Use:
• I understand that any photo captured will be used solely for the purpose of candidate verification and will not be shared externally or used for any other purpose.
• Candidate photos will not be stored and will be securely disposed of after the interview process is complete.
• I consent to the use of geolocation tools for the limited purposes of verifying my location and ensuring interview integrity. This information will be used solely for security and compliance reasons, in accordance with applicable privacy laws.