Chief of Staff

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

The Opportunity:

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

What You'll Own:

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

Writes clean, executive-quality materials under time pressure. Can distill complex inputs into a clear narrative.

AI Fluency

Uses AI tools actively to improve output speed and quality. Has applied AI in actual work, not just experimented with it.

Business Financial Literacy

Understands revenue, margin, and cost structure. Can follow a P&L conversation and connect operational decisions to financial outcomes.

Low-Ego, Company-First Orientation

Operates in service of the CEO, ELT, and company priorities. Shares credit, avoids politics, and does not use proximity to the CEO as personal power.

Nice to Have:

ELT Operating Experience

Has run operating cadences for a leadership team: meeting design, decision logging, follow-through tracking.

Board/Investor Materials

Has owned preparation of board or investor materials end-to-end, without being assigned each step.

AI Agent or Workflow Building

Has built lightweight AI agents or automated workflows, beyond using off-the-shelf tools.

PE or High-Accountability Environment

Has worked in a PE-backed company or similarly high-performance environment with a defined performance horizon.

Benefits Include:

• Medical, dental, and vision insurance options

• 100% employer-paid short- and long-term disability

• Basic life insurance

• 401(k) with 100% company match up to 4%

• Flexible paid personal/vacation time built on trust and accountability

• 10 sick days annually

• 10 company-paid holidays

• 6 weeks paid parental leave

Inclusion and Diversity

Togetherwork is an Equal Employment Opportunity Employer. We value diverse backgrounds, experiences, and perspectives. Employment decisions are made without regard to race, color, religion, gender, gender identity, sexual orientation, disability, veteran status, age, national origin, or any other protected category under applicable law.