Director of Client Success

About Scale to Win

Scale to Win is a fully-remote, progressive, political tech company founded in 2020 by organizing leaders from the Biden/Harris, Bernie 2020, Warren 2020, Bernie 2016, and Hillary for America Presidential campaigns. Our product offerings include Scale to Win Text, our “all-in-one” shortcode and longcode texting tool, and the Scale to Win Dialer, a predictive calling tool. Scale to Win also offers turnkey “We Text” services, where our team builds text campaigns, sends messages, collects data, and ensures compliance on behalf of clients.

We work with more than 3,000 Democratic and progressive campaigns and organizations, driving change. Current and past clients include the Biden-Harris campaign, the Democratic National Committee, the Working Families Party, the AFL-CIO, UFCW, MoveOn, and For Our Future.

Scale to Win is hiring a Product Designer to lead end-to-end design for high-impact product initiatives.

About the Role

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.

Skills & Qualifications

• Seasoned CS Expertise: 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.

• Proven People Leader: 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.

• Master Process Builder: Deep experience creating or heavily iterating on Mutual Success Plans, customer journey maps, and business review frameworks from scratch.

• Data-Informed Strategist: Proficient in leveraging product usage analytics and health metrics to forecast risks, identify expansion opportunities, and drive internal operational alignment.

• Advanced Coach-Player Mindset: 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.

• Agility & Organization: Highly organized, detail-oriented, and capable of driving projects to completion independently in a distributed, remote work environment.

• Mission Alignment: 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.

Note: Meeting every single one of these qualifications is not a requirement. Candidates are considered based on a holistic view of their skills, experience, and potential contributions to our team.

Salary and 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. 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.