Scale to Win, Inc

Role Description Scale to Win is hiring a Product Designer to lead end-to-end design for high-impact product initiatives. The Director of Client Success is a high-impact, strategic "coach-player" role designed for a seasoned Client Success (CS) leader who excels at scaling operations and navigating dynamic environments. You will serve as a critical thought partner to help scale, mature, and lead our Client Success organization. In this role, you will balance high-level strategic leadership with hands-on execution. You will directly manage and mentor a growing team of 3+ Senior Client Success Managers (CSMs), establishing a culture of continuous feedback, empathy, and high performance. Simultaneously, you will own a small, highly selective book of our most strategic, high-value accounts. The ideal candidate understands the architecture of a world-class CS infrastructure, possesses the operational skills to build and refine it, and has a passion for coaching others to deliver stellar client experiences. Core Responsibilities - Team Leadership, Mentorship & Growth (40%) - Manage & Scale Talent: Direct report management for a pod of 3+ Client Success Managers (Levels 1–4). Conduct regular 1:1s, professional development mapping, and equitable performance management. - Culture of Feedback: Act as an intentional coach, delivering actionable, real-time feedback to elevate the team's consultative, troubleshooting, and relationship-management skills. - Onboarding & Excellence: Standardize and oversee the onboarding program for new Client Success (CS) hires (e.g. 30/60/90 day plans), ensuring structured, supportive assimilation into the team's workflows and standards. - Strategic Architecture & Process Development (30%) - Organizational Thought Partnership: Partner closely with the Client Experience leadership to design the future state of the CS org, anticipating scaling bottlenecks and proactively building solutions. - Elevate CS Infrastructure: Co-own, iterate, and optimize foundational CS frameworks. Define standard methodologies for Business Reviews (QBRs/EBRs), design robust Mutual Success Plans, and establish data-driven client health scoring models. - Playbook Blueprinting: Author and execute repeatable playbooks for the entire customer lifecycle (onboarding, growth, retention, and renewal) optimized for the unique rhythms of political, organizing, and nonprofit tech cycles. - Cross-Functional Collaboration: Serve as the strategic voice of the customer internally, synthesizing frontline insights into high-impact product, engineering, and sales feedback initiatives. - Strategic Account Management & Resolution (30%) - Own a Premium Portfolio: Personally manage a small, high-stakes book of business comprising our most complex or strategic accounts, driving their health, platform adoption, and retention. - Executive Presence: Lead high-level engagements, contract renewals, and business reviews for your personal portfolio, translating intricate campaign data into executive-level strategic recommendations. - Friction Resolution: Serve as an escalation point for complex technical or relationship friction points across the department, coaching your team through high-pressure client interventions. Qualifications - 5+ years of direct experience in Client Success or Account Management, with a proven track record of success leading accounts in a software-as-a-service (SaaS) or digital technology environment. - Demonstrated experience in formal people management, with a track record of leading teams of 3+ individuals, fostering psychological safety, and elevating team performance through active coaching. - Deep experience creating or heavily iterating on Mutual Success Plans, customer journey maps, and business review frameworks from scratch. - Proficient in leveraging product usage analytics and health metrics to forecast risks, identify expansion opportunities, and drive internal operational alignment. - Comfort shifting between driving long-term organizational strategy with leadership, mentoring a direct report, and collaborating directly with a client to solve a complex issue. - Highly organized, detail-oriented, and capable of driving projects to completion independently in a distributed, remote work environment. - Deeply aligned with our mission to advance progressive causes, support Democratic candidates up and down the ballot, and empower nonprofit organizers. Nice-to-have Experience - Domain expertise working within, or providing technology to, nonprofit organizations or political campaigns. - Experience with telephony technology: texting and dialing platforms. - Working within tools like: HubSpot, Google Suites, and Slack. Benefits - $160,000 yearly salary (base). As part of our commitment to equity, salaries are non-negotiable. - This role is eligible for a discretionary bonus based on individual, team, and company performance, as determined by the company in its sole discretion. - 401k matching up to 6% after a provisional period. - Ten paid company holidays, two floating holidays, and a week and a half-long holiday break at the end of the year. - Generous paid vacation (up to 24 days a year with time accrued monthly); paid sick leave; paid short-term medical, caregiver, bereavement, and other personal leave. - 16 weeks of paid parental leave and an additional 4 weeks of part-time, fully-paid flex time. This is available to all new parents of any gender, including adoptive parents. - Fully-paid premium, $0 deductible, top-notch medical insurance, as well as dental and vision insurance, for you and your dependents. - Remote working with flexible working conditions, a stipend to support your home office setup, and access to a company computer. - Every employee is invited to donate 25,000 free texts to a non-profit of their choice each year. - To support continued professional growth and development, Scale to Win offers each employee an annual $2,000.00 stipend towards achieving your professional development goals. Travel Expectations This role may require occasional travel to support client meetings, conferences, campaign events, trainings, or company gatherings. Travel expectations will vary based on client needs and campaign cycles, particularly during peak election seasons. Interview Process + Timeline - Submit resume and application - Initial Screen Interview - Hiring Manager Interview - Hiring Assessment - Panel Interview - Co-CEO Meet & Greet - Reference check The position will be open until filled, and applications will be reviewed on a rolling basis. Applicants must be currently authorized to work in the United States on a full-time basis. At this time, we’re unable to sponsor or take over sponsorship of employment visas. Interview Accommodations Scale to Win is committed to providing all candidates a respectful and inclusive interview process. If you require any accommodations to fully participate in the interview process—such as alternative formats, extended time, assistive technology, or other support—please let us know. You can request accommodations by emailing peopleops@scaletowin.com. Scale to Win is an equal opportunity employer. In keeping with our beliefs and goals, no applicant will face discrimination or harassment based on race, color, ancestry, national origin, religion, age, gender, marital domestic partner status, sexual orientation, gender identity, disability status, or veteran status.

Role Description Scale to Win is hiring a Product Designer to lead end-to-end design for high-impact product initiatives. In this role, you will work as a strategic partner to Product and Engineering leadership to architect the product & UX vision. You won’t just define screens - you will define the design strategy for entire product pillars, ensuring our ecosystem is cohesive, scalable, and technically sound. This is a senior individual contributor role with significant ownership and impact. You will partner with the product & design teams to evolve our product design craft, and set the benchmark for user experience at Scale to Win. Core Responsibilities - End-to-end product design (40%) - Own discovery, User Experience design, visual design, prototyping, and delivery for product areas on our roadmap. - Translate highly complex customer problems into elegant solutions that leverage systems thinking. - Design workflows and systems that balance usability, scalability, and technical constraints. - Balance near-term delivery with long-term experience quality. - Design for the long-term product ecosystem, anticipating future technical and product shifts to ensure our systems remain resilient over a 2-3 year horizon. - Customer research & focus (25%) - Be a strong advocate for customer voice and experience, upholding a high standard for problem- and user-focused prioritization and design. - Lead and participate in user research, usability testing, and validation. - Use qualitative and quantitative insights to inform design decisions. - Champion simplicity, clarity, and accessibility. - Cross-functional partnerships (20%) - Work as a strategic partner to Product and Engineering leadership to architect the product vision. - Introduce new tools for design discussions and workshops and model their use through your projects. - Partner with Customer Success, Sales, and other stakeholders to incorporate user insights into product design work. - Product design craft (15%) - Help define and elevate our standards for product design excellence. - Model strong design thinking and systems thinking for the broader team. - Give thoughtful critique and raise the quality bar across initiatives. - Partner with our existing design team to establish the 'Scale to Win' design philosophy—standardizing how we think about user experience, user-centricity, accessibility and AI integration across all squads. Qualifications - 10+ years of experience with a proven track record of leading design for complex problem areas and entire product verticals. - Experience working on B2B SaaS products and on early-stage product design teams. - Passion for customer- and problem-driven product design, with experience teaching others how to take a problem-focused approach. - A developed portfolio demonstrating systems thinking, UX design depth, and mission-critical systems where you navigated significant technical or business ambiguity. - Experience building and contributing to design systems. - Strong product thinking with an ability to leverage business, customer and technical context to inform product design tradeoffs and prioritization. - Experience leading through influence rather than just direct authority; you have a history of winning buy-in for bold, unconventional design directions. Nice-to-have Experience - Experience designing data visualization, fundraising, organizing, political, or messaging products. - Experience in organizing or political work. - Experience leveraging AI-powered tools to accelerate product development workflows. Salary and Benefits - $220,000 yearly salary (base). As part of our commitment to equity, salaries are non-negotiable. - This role may be eligible for a discretionary bonus as determined by the company in its sole discretion. - 401k matching up to 6% after a provisional period. - Ten paid company holidays, two floating holidays, and a week and a half-long holiday break at the end of the year. - Generous paid vacation (up to 24 days a year with time accrued monthly); paid sick leave; paid short-term medical, caregiver, bereavement, and other personal leave. - 16 weeks of paid parental leave and an additional 4 weeks of part-time, fully-paid flex time. This is available to all new parents of any gender, including adoptive parents. - Fully-paid premium, $0 deductible, top-notch medical insurance, as well as dental and vision insurance, for you and your dependents. - Remote working with flexible working conditions, a stipend to support your home office setup, and access to a company computer. - Every employee is invited to donate 25,000 free texts to a non-profit of their choice each year. - To support continued professional growth and development, Scale to Win offers each employee an annual $2,000.00 stipend towards achieving your professional development goals. Travel Expectations - This role may require occasional travel to support client meetings, campaign events, trainings, or company gatherings. Travel expectations will vary based on client needs and campaign cycles, particularly during peak election seasons. Interview Process + Timeline - Submit resume and application. - Portfolio Review. - Initial Screen Interview. - Hiring Manager Interview. - Design Interview. - Panel presentation & Cross-functional interview. - Co-CEO Meet & Greet. - Reference check. - The position will be open until filled, and applications will be reviewed on a rolling basis. - Applicants must be currently authorized to work in the United States on a full-time basis. At this time, we’re unable to sponsor or take over sponsorship of employment visas. Interview Accommodations Scale to Win is committed to providing all candidates a respectful and inclusive interview process. If you require any accommodations to fully participate in the interview process—such as alternative formats, extended time, assistive technology, or other support—please let us know. You can request accommodations by emailing peopleops@scaletowin.com. Scale to Win is an equal opportunity employer. In keeping with our beliefs and goals, no applicant will face discrimination or harassment based on race, color, ancestry, national origin, religion, age, gender, marital domestic partner status, sexual orientation, gender identity, disability status, or veteran status. Above and beyond discrimination/harassment based on “protected categories,” Scale to Win also strives to prevent other, subtler forms of inappropriate behavior (e.g., stereotyping) from ever gaining a foothold. Whether blatant or hidden, barriers to success have no place at Scale to Win.