Chief of Staff

About the role

Togetherwork is a 700-person, PE-backed vertical SaaS company running 30+ platforms across recreation, nonprofit, and community management markets. We are three years into a value creation cycle with a defined exit horizon - and we move fast. The leadership team is experienced and execution-oriented. What they need is a Director, Chief of Staff who will serve as the operating partner to the CEO: owning the executive rhythm, holding senior leaders accountable, and making sure the right decisions get made and followed through on. This is a high-access, high-accountability seat that is visible at the board level. For the right operator, it is one of the best roles in a PE-backed SaaS company. What This Role Is Not: We want to be direct. This is not: A transformation strategist A mini-COO A strategy consultant An executive assistant - even a highly capable one And critically: this is not a role that manages up only. Lateral accountability to ELT, SVPs, and VPs is core to the job. Who We're Looking For: You have driven accountability across senior leaders - not just flagged issues upward, but actually closed the loop. You set the agenda, track commitments, and ensure follow-through without needing the CEO to intervene. You have organizational presence, a low ego, and an instinct to make everyone around you more effective. You also build things. You don't wait to be handed an AI tool - you bring new capability to the team and actively use automation to compress timelines and eliminate manual work. You stay current, and it shows in the quality of your output. Must-Have Qualifications: Candidates who cannot demonstrate the following are screened out: 5+ years of progressive experience in Chief of Staff, BizOps, or executive operations roles Has held senior leaders accountable to commitments in a structured, visible way - not just escalated upward Has driven executive priorities or operations autonomously, without waiting for direction Has applied AI tools in actual work contexts to meaningfully improve speed or quality of output Can speak to business financials (revenue, margin, cost structure) with confidence in an interview Has demonstrated ability to influence from behind the scenes, share credit, and prioritize company outcomes over personal visibility Strong Signals (Not Screen-Outs) Has built board or investor materials - coordinated inputs, managed the timeline, owned the output Has operated in a PE-backed or high-accountability environment with a defined performance horizon Has built or deployed an AI agent or automated workflow - beyond using off-the-shelf tools Prior Chief of Staff, BizOps lead, or Executive Operations role at a comparable company

Responsibilities

• ELT Operating Rhythm & OKR Accountability
• Design and own ELT meeting cadence end-to-end: agenda, pre-reads, facilitation, decision logging, and follow-through tracking
• Drive CEO OKR execution - keep the ELT aligned on priorities, track progress, and surface risk before it compounds
• Own ELT OKR alignment: each function's objectives connect to company-level goals, gaps are visible, and owners are on the hook
• Hold senior leaders accountable to commitments between meetings - without requiring CEO escalation
• Drive pre-meeting alignment so ELT time is used for decisions, not information sharing
• Board & Executive Material Preparation
• Own the preparation calendar for board meetings, investor check-ins, and executive materials
• Coordinate across functions to consolidate inputs without creating bottlenecks
• Ensure materials reflect the exit narrative: EBITDA performance, operational milestones, people story
• Cross-Functional Coordination
• Identify and resolve misalignment across ELT workstreams before it reaches the CEO
• Own the ELT decision log and ensure decisions are communicated and implemented
• Surface OKR conflicts and interdependencies before they become execution blockers
• Serve as an extension of the CEO's intent - not a separate power center
• AI-Enabled Executive Operations
• Apply AI tools and automation to streamline executive operations, board prep, meeting synthesis, and follow-through tracking
• Stay ahead of the AI capability curve and bring relevant tools to the ELT without being asked
• Actively use AI to compress timelines on deliverables
• Capabilities That Matter Most:
• Required:
• Accountability Management
• Can hold senior leaders to commitments without formal authority and without escalating to the CEO. Uses structure and relationships, not hierarchy.
• Executive Presence
• Comfortable in rooms with VPs and SVPs. Can push back directly and professionally. Operates through trust, not title.
• Proactive Execution
• Drives priorities without being told. Builds the agenda, follows up on decisions, and closes loops across functions.
• Structured Communication

Benefits

Additional Information

Chief of Staff Location: Austin, TX (Hybrid required 3 days per week) Reports To: CEO Compensation: Competitive base + bonus + benefits

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