Senior Associate of Strategy & Business Operations

Gainsight

1d•Remote

About The Position

We’re building the AI-driven future of customer success, from retention to growth! Gainsight is the AI-powered retention engine behind the world’s most customer-centric companies. The Gainsight CustomerOS platform orchestrates the customer journey from onboarding to outcomes to advocacy. More than 2,000 companies trust Gainsight’s applications and AI agents to drive learning, adoption, community connection, and success for their customers. To explore how our suite of solutions is shaping the future of customer success, check out the link. About This Role: We’re looking for a full-time Senior Associate of Strategy & Business Operations to join our Corporate Services team reporting to the VP, Strategy & Business Operations. This role is a remote role based in The United States. In this role, you’ll play a key role in driving company-wide strategy and operational excellence by owning planning cycles, tracking performance, and executing high-priority cross-functional initiatives in partnership with executive leadership. This is a great opportunity for someone who thrives in a high-impact, ambiguous environment and enjoys working cross-functionally with teams like the CEO, CFO, CRO, Corporate Marketing, and Business Unit GMs. The ideal candidate brings strong skills in strategic planning, stakeholder management, and operational execution.

Requirements

3+ years of relevant experience and a Bachelor’s degree (or equivalent combination of education and experience).
Experience in private equity / venture capital, strategy, business operations, management consulting, or a Chief of Staff role, with demonstrated ability to drive complex, cross-functional work in a fast-moving environment.
Strong structured thinking and communication skills, with the ability to synthesize ambiguous information into clear recommendations and crisp executive-ready materials.
High degree of analytical fluency, including comfort building financial models, synthesizing data from multiple sources, and translating analysis into executive-level insights.
Proficiency in data analysis and visualization tools, as well as Excel and PowerPoint; able to build and present executive-grade materials independently.
Strong executive presence and interpersonal skills, with the ability to engage credibly with C-suite leaders, manage senior stakeholders across organizational boundaries, and exercise sound judgment and discretion in a high-visibility role.
Comfortable operating with significant ambiguity in a lean team environment, with the self-direction and resilience to define structure where it doesn’t yet exist.
Exceptional written communication skills, with demonstrated experience developing executive-level materials including board presentations, internal announcements, and leadership messaging across a variety of audiences and formats.
A naturally curious and intellectually humble professional who brings a learner's mindset to every problem, actively seeks feedback, and adapts quickly. Equally comfortable challenging their own assumptions as they are operating in unfamiliar territory.

Nice To Haves

Familiarity with customer success, post-sale SaaS, or the broader CS technology landscape.
Experience in SaaS, enterprise software, or a high-growth technology company.
Experience owning or significantly contributing to operating cadence design, OKR/V2MOM/goal-setting processes, and/or annual planning cycles at an organizational level.

Responsibilities

Own and continuously improve the company’s core operating cadence, including quarterly business reviews, V2MOM/OKR setting, mid-cycle tracking, end-of-cycle reporting, and executive team rhythms.
Drive high-priority, cross-functional strategic initiatives on behalf of the CEO, acting as program manager with end-to-end accountability for coordination, stakeholder alignment, and delivery.
Coordinate the annual planning process end-to-end in partnership with Finance, translating strategic priorities into resource and investment decisions for CEO and CFO review.
Own the narrative and coordination for board decks, investor materials, and key executive presentations, ensuring the CEO is prepared and aligned for high-stakes internal and external moments.
Build and maintain the data layer that supports executive decision-making, including performance dashboards, KPI tracking, and business reviews synthesizing cross-functional data for the CEO and CFO.
Serve as a shared strategic resource to the Business Unit GMs and functional leaders, supporting cross-functional coordination and ensuring executive visibility on issues that span organizational boundaries.
Provide analytical and project management support on M&A or strategic partnership evaluations as needed.
This role requires availability beyond standard business hours. Responsiveness to executive leadership, including evenings and weekends when business-critical situations arise.
This role will require occasional travel for team meetings, training, or company events.