Application Guide

How to Apply for Staff Product Designer

at Scale to Win

🏢 About Scale to Win

Scale to Win is a fully remote progressive political tech company that powers over 3,000 Democratic and progressive campaigns with texting and dialer tools. Founded by organizing leaders from major presidential campaigns, it offers a mission-driven environment where your design work directly impacts elections and social change.

About This Role

As Staff Product Designer, you will own end-to-end design for high-impact initiatives, from discovery to delivery, shaping products used by campaigns like Biden-Harris and the DNC. You'll lead customer research, establish design standards, and partner cross-functionally to drive product strategy in a fast-paced, mission-focused startup.

💡 A Day in the Life

You might start your day with a standup with product and engineering to align on sprint goals, then dive into user research sessions with campaign staff. Afternoons could involve sketching flows for a new feature, refining design system components, and reviewing prototypes with stakeholders before iterating based on feedback.

🎯 Who Scale to Win Is Looking For

  • Has 10+ years leading design for complex B2B SaaS products, ideally in early-stage or startup environments.
  • Demonstrates a strong portfolio with systems thinking, UX depth, and experience navigating technical and business ambiguity.
  • Has built or contributed to design systems and can influence through leadership, not just execution.
  • Passionate about progressive politics and understands the unique needs of campaigns and organizing teams.

📝 Tips for Applying to Scale to Win

1

Tailor your portfolio to highlight B2B SaaS projects with complex workflows, especially those involving data-heavy interfaces or real-time collaboration.

2

Include a case study that shows how you navigated ambiguity—e.g., undefined requirements or technical constraints—and drove design decisions.

3

Mention any experience with design systems you've built or scaled; if you have a public system, link to it.

4

Research Scale to Win's product (e.g., Spoke, ThruText) and reference specific features or pain points you'd improve.

5

In your cover letter, explicitly connect your design philosophy to progressive political impact—show you understand the stakes.

✉️ What to Emphasize in Your Cover Letter

['Your ability to own end-to-end design in early-stage, fast-moving environments.', 'Experience with B2B SaaS and design systems, with concrete examples.', 'Understanding of progressive campaigns and how design can amplify organizing efforts.', 'Leadership in cross-functional teams and influencing without authority.']

Generate Cover Letter →

🔍 Research Before Applying

To stand out, make sure you've researched:

  • Read about Scale to Win's founding story and their key clients (Biden-Harris, DNC, Working Families Party).
  • Explore their open-source tools (e.g., Spoke) to understand their design language and UX patterns.
  • Review recent blog posts or press about how their tools are used in campaigns (e.g., during the 2024 election cycle).
  • Understand the competitive landscape (e.g., Hustle, Mobilize) and identify gaps Scale to Win's design could fill.
Visit Scale to Win's Website →

💬 Prepare for These Interview Topics

Based on this role, you may be asked about:

1 Walk me through a time you led design for a complex, ambiguous problem. How did you define the scope?
2 How would you approach building a design system for a suite of campaign tools used by non-designers?
3 Describe a situation where you had to advocate for user needs against business or technical constraints.
4 How do you balance speed and quality in a startup environment where campaigns have urgent deadlines?
5 What metrics would you use to measure the success of a design change in a political texting tool?
Practice Interview Questions →

⚠️ Common Mistakes to Avoid

  • Don't submit a generic portfolio without B2B or complex workflow examples—they'll see it as misaligned.
  • Avoid focusing solely on visual design; emphasize UX strategy, research, and systems thinking.
  • Don't ignore the political context—failing to mention progressive impact or campaigns signals lack of fit.

📅 Application Timeline

This position is open until filled. However, we recommend applying as soon as possible as roles at mission-driven organizations tend to fill quickly.

Typical hiring timeline:

1

Application Review

1-2 weeks

2

Initial Screening

Phone call or written assessment

3

Interviews

1-2 rounds, usually virtual

Offer

Congratulations!

Ready to Apply?

Good luck with your application to Scale to Win!