Chief of Staff, Philo
$250-300k
+ company stock options
Senior and Expert level
New York
Office located in Brooklyn, NY
Live TV streaming service
Open for applications
Live TV streaming service
201-500 employees
B2CEntertainmentDigital MediaVideo
Open for applications
$250-300k
+ company stock options
Senior and Expert level
New York
Office located in Brooklyn, NY
201-500 employees
B2CEntertainmentDigital MediaVideo
Company mission
To provide affordable and accessible television streaming services to everyone.
Role
Who you are
- 8+ years of experience in strategy, chief of staff, business operations, or executive program management roles
- Experience in media, streaming, or consumer subscription businesses — you understand the economics of subscriber acquisition, retention, and engagement, and you can speak the language of this industry from day one
- Experience working directly alongside C-suite or senior VP-level leaders in a high-trust, high-proximity environment
- Demonstrated track record of owning strategic research, synthesis, and analysis — not just coordinating it: structuring ambiguous problems, working with data, and turning it into decision-ready framing for leadership
- Experience designing or improving operating rhythm and planning processes — leadership reviews, planning cycles, goal-setting frameworks — in a fast-moving environment
- Exceptional written communication: research briefs, agendas, decision framing, and async updates are the core work product of this role, and the quality of your thinking shows up in the quality of your writing
- The instinct to know when to solve a problem yourself and when to sharpen it and hand it back — you can unstick a cross-functional issue without becoming its permanent owner
- Confident but not territorial: strong enough to push back and offer a point of view, secure enough to support rather than lead, and clear-eyed about where your role ends and others' begins
- High discretion and professional judgment — this role sits close to sensitive conversations including board materials, personnel, strategy, and transactions
- Comfort with ambiguity: the operating model at Philo was rebuilt this year, and this person will help build and refine infrastructure that is still taking shape
- Meticulous where it counts — board decks go to a board, leadership agendas go to a dozen senior leaders, and the work that goes out from this role needs to be right
- Experience supporting a strategic transaction process (M&A, fundraise, partnership) a plus
What the job involves
- Philo launched a significant operating reset in 2026 — new leadership structure, new meeting cadence, and a sharper focus on strategic clarity and accountability. A dedicated Chief of Staff is a core part of that reset
- This is a strategic Chief of Staff role. It exists to make Philo's most senior leaders more effective— not to absorb the operational work of the business. The right person sharpens the thinking, structures the agenda, keeps leadership aligned, and ensures that decisions made in the room actually happen
- Execution of the company's work lives with the functional and program management teams. This role makes sure those teams have the right direction, the right inputs, and the right forums to do it
- The role reports to the SVP of Strategy & Operations and operates in service of the Strategy & Operations, COO, and CEO functions, with lighter-touch support for the CFO. It anchors to Strategy & Operations initially (~50% strategic and analytical agenda), supports the company operating rhythm (~35%), and provides CEO/CFO executive support including board coordination (~15%)
- Just as importantly, this is a hands-on role. We're looking for someone with high ownership and low ego—someone who sees no task as beneath them
- One day you may be framing a strategic recommendation for the executive team; the next you may be building the analysis, writing the memo, creating the deck, or coordinating the follow-through needed to get the work across the finish line. Success comes from a willingness to both think strategically and execute exceptionally
- Strategic Research & Analysis
- Conduct research and analysis at the direction of the SVP of Strategy & Operations to support strategic planning, competitive intelligence, growth opportunity evaluation, and packaging and pricing decisions
- Synthesize inputs from across the business — data, external research, vendor outputs — into clear, decision-ready framing for the executive leadership team. Build and maintain awareness of the competitive landscape, market trends, and strategic context relevant to Philo's key bets
- Structure ambiguous problems, build a clear point of view, and present it concisely to senior leaders
- Planning & Goal-Setting Process
- Partner with the executive leadership team to coordinate annual planning, quarterly prioritization, and the development of company goals and strategic initiatives
- Help develop implementation plans, milestones, and success metrics for new initiatives — ensuring strategic decisions translate into clear plans with owners
- Support the design and ongoing improvement of planning processes, goal-setting frameworks, and accountability mechanisms
- Ensure the right people are in the room at the right points in the planning cycle, and that outputs are clearly documented and communicated
- Drive cross-functional alignment by ensuring every strategic initiative has clear objectives, success criteria, accountable owners, defined decision rights, and an agreed execution plan, resolving ambiguity where ownership or accountability is unclear
- Operating Rhythm & Leadership Alignment
- Support SVP of Strat and Ops with owning the weekly business performance meeting agenda: collect inputs, ensure anomalies are pre-researched and flagged before the meeting, coordinate pre-reads, and keep the meeting focused on diagnosis and action — not status recaps. Develop and maintain a consistent cadence of KPI analyses that explain performance trends, uncover root causes, and highlight opportunities for action
- Support the COO in running the senior leadership team: prep agendas, distribute pre-reads, and track decisions and commitments through the operating infrastructure
- Coordinate leadership async updates after key decision-making meetings — ensuring decisions, priorities, and next steps are clearly communicated to the right people
- Own the leadership operating calendar — right meetings at the right cadence, right people in the room, preparation requirements communicated in advance
- Maintain Philo's core operating infrastructure: decision logs, commitment trackers, and related systems that keep the leadership team accountable
- Ensure executive review meetings have clear agendas, decision objectives, and expected outcomes. Partner with cross-functional leaders to distill materials into concise executive summaries and drive alignment on decisions, owners, and next steps
- Cross-Functional Problem Solving
- Act as an extension of the executive leadership team to identify opportunities, resolve operational challenges, and remove barriers to execution across the organization
- Partner with the Programs organization on cross-functional initiatives: this role unblocks and aligns at the leadership level; sustained program delivery stays with Programs
- Executive Forums & High-Stakes Moments
- Facilitate leadership offsites, annual planning sessions, company bi-annual gathering, and strategic reviews — owning the design, preparation, and follow-through for forums that shape company direction
- Support board meeting preparation: coordinate slide ownership, track contributors, manage review timelines, and ensure materials are complete and polished
- Coordinate preparation for other high-stakes leadership moments — all-hands materials, due diligence requests, executive briefings — where quality and timing matter
- Own async communication when key leaders are offline, ensuring nothing falls through
Our take
Streaming services offer cheaper options than cable TV packages, but prices are beginning to rise. This is partly due to packages beginning to bundle costly sports and other media packages that viewers do not necessarily want.
Philo offers a streaming service that aims to provide a streamlined selection of channels as an affordable, yet comprehensive, viewing option. The streamlined and high-quality channel offerings are available to viewers at $30 per month, a price significantly lower than standard cable subscriptions, with the base option including around 60 live channels and over 75,000 on-demand offerings.
Philo stands out through features like a co-viewing service that lets up to three people watch the same program together, enhanced cloud DVR functionality, and expanded compatibility with smart TVs and popular streaming devices such as Roku, Fire TV, and Apple TV. These updates demonstrate Philo's continued focus on accessibility, user experience, and cost-effective entertainment.
Steph
Company Specialist at Welcome to the Jungle
Insights
Top investors
10% employee growth in 12 months
Company
Funding (last 2 of 7 rounds)
Aug 2020
$50m
SERIES D
Jul 2018
$41.4m
SERIES C
Total funding: $155.7m
Company HQ
Telegraph Hill, San Francisco, CA
Leadership
Andrew McCollum
(CEO)Studied Computer Science at Harvard before co-founding Facebook. Joined Philo in 2014 and has acted as CEO since.
Salary benchmarks
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