Product Manager

About Headway

Founded in 2015, Headway was born out of a passion to bring entrepreneurial ideas to market and keep them there. We work holistically with our client partners as a true extension of their product team, not just as an execution arm of their business. If we see something broken, whether that’s a workflow, a marketing or messaging strategy, or a needless feature, we speak up, and our clients trust us to help them fix it.

Because we’re more than just designers, developers, and product strategists, we achieve results that bring successful long-term partnerships and trusted referrals. We help entrepreneurs and corporate innovators build a business ― not just an app. Our approach to validating ideas and building sustainable business models has been a catalyst for our growth. In 2020 we were honored to be named to the Inc. 5000 at #918 and in 2022 at #2765. This approach, coupled with realistic and incremental software releases, results in a friendly, fun, and collaborative atmosphere where our colleagues and clients both have room to learn and grow.

View our case studies and see how our clients talk about our approach.

If you’re a podcast fan, check out Seaworthy, where we explore ways to help companies grow and scale their business and ideas, Even Keeled, a podcast about the craft of creating software and effective development teams, and Exploring Product, a show where we go behind the scenes on what it really takes to bring a new product to market.

We’re actively engaged with our community through various live streams and videos to help startups and product teams reach their goals. We’re excited about what we’ve achieved in the last six years, but we’re just getting started. We need your help to take us to the next level!

As a Product Manager at Headway, you are responsible for executing within the Headway product process with a focus on client and user needs, including:

Collaborating with Clients, Stakeholders, Designers, and Developers to make awesome products customers love.
Working with our Head of Product Strategy and Product Team to improve our team’s best practices
We use a dual-track agile methodology that bridges the gap between discovery and delivery to make more effective products that are informed by experiments.

Stakeholder management:

Aligning with clients on long-term priorities & product success metrics
Track & communicate progress
Facilitating workshop sessions to help the team & stakeholders move fast
Identifying risks to the product’s success and being vocal about how we might be able to reduce the risk


Mapping out the customer journey & key flows
User story mapping
Customer Personas
Customer Research: Usability Testing
Prototyping solutions in collaboration with designers and tech leads
Solution Design / Wireframes

Delivery Management:

Project Management
Roadmap & release planning
Managing the product backlog & roadmap
Planning release prioritization using user story mapping focused on customer outcomes
Agile Team Experience: Sprint & Release Planning, User Stories, Managed Backlog, Daily Standups, Retrospectives
User story creation
Acceptance Testing
Storypoint Estimation (Epics + Stories)
Helping the team iterate rapidly to maximize learning in fast feedback loops


Data models, entity diagrams
Systems flows, decision trees


You are:

Fast Learner, Absorbs new domains quickly
Able to transition from High-level thinking to Low-level execution
Confidence in Presenting
Withholds Judgement
Systems Thinking
Sees Patterns
Go-Getter, Takes initiative, Ownership mentality
Organized, Disciplined
Continuous Learner
Humble, Seeking Personal Growth
Team Player & Collaborative
Experience in Autonomous Teams
Ready to go with Google Suite, Slack, etc.


Rapid Delivery & Experimentation:

Feature Flags
Continuous Delivery / DevOps
Lean Startup Experience
Designing experiments around key customer behaviors.

Data & Analytics:

Customer Segmentation
Analytics Pipelines, etc.
Mixpanel, Amplitude, Looker, etc.
Intercom, etc.
Data Visualization
Data Transformation


Opportunity Trees
Continuous Discovery
Customer Interviews, Empathy
Risk Assessments / Assumption Mapping
Finding bottlenecks & opportunities to improve customer experience
Customer Segmentation, Personas
Problem Space vs. Solution Space
Unit Economics
Business Models

Behavior-Driven Engagement:

Marketing Tech
Omni-channel Automations
Intercom, etc., etc.

A Day in the Life

During a typical work week, our crew members enjoy a balanced assignment of 35 hours on client projects with the ability to invest the other 5 hours on a combination of individual goals and team meetings. Twice a year, we take a full week away from client work to focus on team goals and internal project initiatives. These weeks alternate between a retreat-style destination that encourages team bonding and goal setting, and a more focused week-long design and development sprint at our primary office in Wisconsin. Check out some of our team week recaps and years in review to get a feel for how much fun it is to work at Headway!

What Does Success Look Like?

During your first 2-4 weeks at Headway, you’ll receive extensive on-the-job training and assignments. This training covers the fundamentals of our core product processes and workflows, our core technologies, the way we delegate tasks within a product team, customer research strategies, validation approaches, tips for successful client interactions, and much more.

You’ll have dedicated pairing time scheduled with various colleagues to cover different skills, and we’ll even participate in several mock client sessions so you’ll be confident going into your first client engagement. You’ll be fully supported along the way. You’ll join a product team, and will soon be contributing to designing and building awesome digital products. Welcome aboard!

Ongoing Support

Each week, you’ll meet with your team lead to ensure that you have the time and attention you need to be successful. Your needs and questions will always come first in this meeting, but other topics discussed include:

Individual quarterly goal progress
Project status / team issues / weekly retro
Individual responses to our weekly team health questionnaire

Quarterly and Annual Reviews

In addition to weekly touchpoint meetings, more formal quarterly reviews are scheduled to discuss successes and areas for growth identified over the last 3 months. We have annual performance assessments and salary reviews, though we reserve the right to provide a merit-based pay raise at any time. Most crew members achieve between a 2% and 5% raise each year within their same role, but bigger jumps are possible when roles or responsibilities increase. We’re here to grow with you sustainably over the long term.

Experience and Results At Every Level

With an experienced leadership team encompassing design, development, sales, marketing, product, and operations, Headway is poised for an amazing 2021. Our business is guided by EOS and we have strong processes, documentation, and people to support your growth and development. As they say, “Train people well enough so they can leave, treat them well enough so they don’t want to.” For more on that, check out our benefits!

Why Should You Apply?

Work on exciting projects in the latest tech across a variety of industries including the following:Healthcare and Fitness
Financial Technology
Logistics and Supply Chain
Social and Communication
Collaborate with colleagues and clients directly to ship features that users love.
Work with appreciative clients who seek out and value your input and feedback.
Strong leadership and top-notch colleagues to help you realize your full potential.
Career growth and leadership opportunities.

Key Benefits

3 weeks of PTO & Sick Time available immediately.
4 weeks of paid parental leave.
1 week of additional time off during the winter holiday season.
100% of health care and dental premiums paid for you and all your dependents.
Up to a 4% matching 401k contribution based on your dollar contribution.
$6,000 hardware onboarding budget including $2,500 to spend however you like.
$2,500 annual education and conference budget.
Quarterly profit-sharing bonus plan.

The Hiring Process

If after we review your application and we choose to move forward, the following interviews will typically take place over the course of 1-3 weeks (depending on scheduling):

Work history and aspirations chat with our People and Team Strategist.
Skills and performance discussion with a Product Lead.
Skills assessment.
Group interview with several members of the Headway team.
EQi and Kolbe assessment exercise.


You live by our Guiding Manifesto and embody the core values of Headway.
You are open to criticism from your team and are always eager to learn and to share knowledge.
You have the ability to think big while being detail-oriented and delivery-focused.
You are self-motivated and able to deal with pressure and work well in a fast-paced environment.
You have an outgoing, personable, and sociable attitude.
You have the initiative to solve challenges, meet goals, and set new directions based on data.
You are capable of inspiring colleagues and clients.
You have a passion to create useful and valuable solutions.
You prioritize and attend our twice-annual team weeks on-site at our primary office in Wisconsin, or at an awesome TBD destination.

Next Steps

If this sounds like you, we’d love to have you apply! We’re a remote-first company so this position is open to developers local to the Green Bay, WI area, and anyone living in and able to work in the US.

Tagged as: Remote