Headway logo

Product Strategist

Founded in 2015, Headway was born out of a passion to bring entrepreneurial ideas to market and keep them there.

Headway

Icons/design/feather/users

11-50

Founded in 2015, Headway was born out of a passion to bring entrepreneurial ideas to market and keep them there.

We help entrepreneurs build businesses - not just features.

We work holistically with our client partners as true product teams. We bring an ownership mentality to design, validation, and building great digital products. Our clients trust us because we focus on addressing risk head-on, learning quickly, and creating awesome products that customers love.

Our product strategists, designers and developers create incredible products that bring successful long-term partnerships and trusted referrals.

This approach, coupling an experimental-mindset 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.

See how our clients talk about our approach and check out some of the recognition we’ve received so far. Discover how we show our clients appreciation with unique holiday gifts each year. Or, if you’re a podcast fan, check out Seaworthy, where we explore ways to help companies grow and scale their business and ideas. We’re excited about what we’ve achieved in the last few years, but we’re just getting started. We need your help to take us to the next level!

Position Description

At Headway, as a Product Strategist


You'll be bringing new digital products to life - working with a small multi-disciplinary team of designers, developers, and other talented product people.


Working closely with our team and clients, you will be validating product ideas, finding market opportunities, designing solutions, challenging assumptions, running experiments, presenting to stakeholders, and collaborating with the full product team to make new products a reality.


You'll help make decisions on product direction and stand up for creating value for both customers and the business.

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. Each quarter, 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 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.

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:

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

Quarterly & Annual Reviews


In addition to weekly touch point 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.

Why should you apply?


  • Work on exciting projects in the latest tech across a variety of industries including: Healthcare, FinTech, Education, Personal Growth & Training, Lifestyle & Social
  • Collaborate with colleagues and clients to create products customers 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


Work, Play, & Everything in between


Friday Team Lunches


Every week we meet as a team to share personal and professional wins while we break bread.

Onboarding Package


A $5,000+ hardware package; MacBook Pro, peripherals, and more!

Continuous Learning


35 hrs/week for client work and 5 hrs/week for investment time. We also host workshops and meetups.

Horizontally Structured


We all grow together. Have a clear path for professional development.

Flex Time


Work where you work best. We're remote-first. Need to take a break during the day? No problem.

Healthcare, Dental, & Vision


We cover 100% and offer PPO or HSA matching plans, and cover 100% of your dental insurance. We also offer vision coverage for a split cost.

Life & Disability Insurance


All full-time employees receive disability (Short and Long Term) and life insurance. (Term Life and AD&D) We also extend the opportunity for each employee to purchase additional term life and AD&D for yourself, spouse, and children.

Parental Leave


2 Weeks PTO, unlimited UTO thereafter.

Holiday Refresh


Headway HQ has a paid rest period between Christmas and the New Year.

Bi-Annual Retreats


Growing together and having fun. Hiking, snowboarding, hacking, team building, relaxing.

PTO


4 weeks of paid time off every year (vacation, sick-time, and holiday refresh).

Swag & Gatherings


Get all the free gear you need! We also host gatherings, meetups & workshops.

401K


We match 100% of the first 3%, and 50% of the next 2%. If you contribute 5%, we contribute 4%.

The Hiring Process


If after we review your application and we choose to move forward, you will be moving along this path:

  • Skills questionnaire
  • Work history and aspirations chat with our People and Team Strategist
  • Skills and performance interview with our Head of Product Strategy & Innovation
  • Take-home exercise / assessment
  • Team fit discussion with a member of the product strategy or design team

Responsibilities


As a Product Strategist at Headway, you are responsible for executing within the Headway product strategy 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 & Innovation to improve Product best practices
  • Owning Customer Discovery for client engagements, including: customer interviews, surfacing and capturing key insights, synthesis and affinity mapping, personas, etc.
  • Defining customer segments
  • Aligning with clients on product success metrics
  • Prototyping solutions in collaboration with designers and tech leads
  • Mapping out the customer journey & key flows
  • Designing business models
  • Finding bottlenecks & opportunities to improve customer experience
  • Facilitating workshop sessions to help the team & stakeholders move fast
  • Planning release prioritization using user story mapping focused on customer outcomes
  • Managing the product backlog & roadmap
  • Designing experiments around key customer behaviors
  • Identifying risks to the product's success and being vocal about how we might be able to reduce the risk
  • Helping the team iterate rapidly to maximize learning in fast feedback loops

Requirements


  • Fast Learner, Absorbs new domains quickly
  • Customer Research, Customer Interviews, Empathy
  • Customer Journey maps, Personas
  • Problem Space vs. Solution Space
  • Confidence in Presenting
  • Withholds Judgement
  • Systems Thinking
  • Sees Patterns
  • Agile Team Experience: Sprint & Release Planning, User Stories, Managed Backlog, Daily Standups
  • Solution Design / Wireframes
  • Prototype Feedback / Usability Testing
  • Go-Getter, Takes initiative, Ownership mentality
  • Organized, Disciplined
  • Continuous Learner
  • Self-Aware
  • Humble, Seeking Personal Growth
  • Team Player & Collaborative
  • Ready to go with Google Suite, Slack, etc.

Bonus Requirements


  • Group Facilitation / Workshops
  • Stakeholder Management / Account Management
  • Lean Startup Experience
  • Risk Based Prioritization
  • Running Experiments
  • Startup Experience
  • Sales Experience
  • Value Proposition Design
  • Marketing Tech
  • Jobs to be Done
  • Market Sizing
  • Competitive Analysis
  • Usability Testing
  • Unit Economics
  • Cohorts
  • P&L / Revenue Models
  • Data Analytics & Visualization
  • Data Transformation / SQL
  • Software development background
  • Experience in Autonomous Teams

About this role

January 1st, 2022

January 17th, 2021

Full Time

-10.00 -10.00
-9.50 -9.50
-9.00 -9.00
-8.00 -8.00
-7.00 -7.00
-6.00 -6.00
-5.00 -5.00
-4.00 -4.00
-3.50 -3.50
-3.00 -3.00
-2.00 -2.00
14.00 14.00

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About Headway

Learn about Headway and their company culture.

View company profile

We partner with startups & corporations to create successful software through business and product strategy, design, and development.

We'll help you validate your ideas, define your business strategy, design and build your product, and help you grow your business with a plan that works.

Don't just build an app, build a business.

We’re looking for talented & open-minded creatives to help us build software that makes a difference.

What’s it like to be a part of our crew?

While many of us are developers and designers, we're all consultants too. Each crew member has unique experiences and skills that can help clients and Headway chart a better course for smooth sailing.

What you should know

  • Flexible and Accountable: Our crew works locally, remotely, and even has the ability to flex their hours during the week. The key to our success is that we are all held accountable to get things done no matter where life takes us. Trust makes it all possible.

  • You Be You: We're all human here at Headway. We laugh together and lift each other up. Our crew isn't afraid to speak their mind but also maintains respect for others. We encourage you to pursue the things you daydream about. Most of the crew have side projects going on and they love talking about them.

  • The Ego: There's nothing worse than making something you don't believe in. When we design or build anything, we get excited about it together and stand behind it. Our pride lands fully in what we can do for our clients. We're not attached to our own designs, and any ego is left at the door.

  • Every Crew Member Matters: Listening is how progress can begin. We believe that everyone and their ideas deserve to be heard. We're not just cogs in a machine here - we're real people working together to build products that serve a purpose.

  • Always Room For Fun: We're serious about having fun just as much as we are about building products. When you're here, you'll probably hear dad jokes, see lots of memes, and hear interesting stories from the whole crew. We even host team retreats and community events to give everyone a chance to connect and grow together.

  • Keep It Real: Integrity seems to get thrown around a lot in business language, but we definitely live it here. We hold ourselves to a high standard when building products because it's what matters. We're tired of other people selling snake oil just to make a buck.

Tech stack

Learn about the technology and tools that Headway uses.

View tech stack

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