Chief of Staff

The Chief of Staff Association has been retained by an AI-first business process outsourcing (BPO) company targeting Banking, Financial Services, Digital Native, and Utilities sectors. The business is PE-backed and at an inflection point, building its partner ecosystem, entering new markets, and laying the foundation for inorganic growth.

Chief of Staff Role

Reporting to the CEO, the Chief of Staff will be a senior strategic partner to the CEO. This role combines governance and investor interface, market strategy and program incubation, and end-to-end corporate development into one high-leverage role at the heart of the business. The business is at an inflection point, building its partner ecosystem, entering new markets, and laying the foundation for inorganic growth. The Chief of Staff will be the CEO's most trusted day-to-day partner, acting as a force multiplier across governance, strategy, and deal-making. With a strong executive leadership team already in place, this role is explicitly not an executive-administration function; it is a strategic and operational leadership role.

This is a full-time, remote-first position, with periodic travel (approximately 10%) to company offices and board/investor meetings.

Responsibilities

The Chief of Staff's responsibilities span three major pillars: CEO Force Multiplier, Strategy, and Corporate Development.

Pillar 1: As a force multiplier, the CoS owns the CEO's strategic decision-making infrastructure, not their diary. Focus is on governance design, investor relationships, and organizational intelligence.

• Own the CEO's strategic decision-making infrastructure: decision log, priority stack, and cross-functional accountability framework

• Design and run the leadership team's operating rhythm: agenda-setting, pre-reads, and outcome tracking for senior leadership sessions

• Establish standard operating procedures and playbooks to enable change management

• Ensure critical decisions have the right stakeholders, data, and timing, surfacing blockers before they become CEO-level emergencies

• Serve as the CEO's proxy in cross-functional forums where presence is needed but CEO bandwidth should be preserved

• Own the primary working relationship with the PE sponsor: active engagement on strategy and value creation, not just reporting

• Build and maintain the value creation plan: initiative design, owner accountability, EBITDA bridge, KPI development, and milestone tracking

• Support the CTO and technology team in managing AI progress, including explaining progress against the AI roadmap and prioritization

• Prepare and deliver quarterly board packs, owning the narrative as much as the numbers

• Monitor alignment across the senior leadership team, surfacing tensions, role ambiguities, or strategic misalignments before they become structural problems

• Support the CEO in holding the leadership team accountable to agreed priorities without creating a bottleneck

• Own and drive strategic initiatives that are CEO-priority but lack a natural functional home, typically cross-cutting programs requiring orchestration across the CHRO, CFO, CRO, and Head of Ops

• Manage program governance for early-stage strategic bets, keeping workstreams moving and the CEO informed at the right level of detail

Pillar 2: Lead the strategic planning process, drive new market analysis, and incubate early-stage strategic programs from hypothesis through to execution.

• Own the strategic planning process: market sizing, competitive positioning, initiative prioritization, and financial roll-up

• Build and maintain competitive intelligence on AI-first BPO peers, emerging AI platforms, and disruptive tools across target verticals

• Translate the strategic plan into functional priorities and measurable KPIs for each business unit

• Lead systematic market-entry analysis for new verticals and geographies: TAM/SAM/SOM, competitive dynamics, customer segmentation, and pricing benchmarks

• Develop and stress-test the right-to-win hypothesis for each market, articulating differentiation versus incumbents and AI-native competitors

• Drive PE fund targeting research and scoring for the top-50 fund GTM program

• Build market maps and ecosystem analyses to inform partnership and M&A priorities

• Develop the partner program strategy in partnership with the CRO: framework, partner tiers, economics, onboarding, and enablement

• Design new pricing models in partnership with the CFO: outcome-based pricing, AI efficiency gain-sharing, and competitive benchmarking

• Lead early-stage incubation of other CEO-priority strategic programs, from hypothesis through business case to launch

• Build buy-versus-build-versus-partner frameworks for key capability gaps

Pillar 3: Own the inorganic growth agenda end to end, from thesis development and pipeline management through diligence, negotiation, closing, and post-acquisition integration.

• Own the M&A pipeline: thesis-led target identification, market mapping, and prioritization across capability, geography, and vertical dimensions; the PE sponsor will support through a Corporate Development Director

• Source proprietary opportunities through CEO, investor, banker, and ecosystem relationships

• Build and maintain financial models, valuation analyses, and synergy assessments for priority targets

• Prepare investment theses and screening memoranda for CEO and board evaluation

• Lead end-to-end deal execution, managing diligence workstreams across operations, technology, finance, legal, HR, and tax

• Drive deal structuring, term negotiation, and closing in partnership with external advisors and counsel

• Manage banker, advisor, and target relationships, maintaining clear escalation paths to the CEO and board

• Prepare investment approval materials for the PE sponsor: investment memoranda, valuation bridge, and risk assessment

• Design and own the integration playbook: governance structure, workstream framework, synergy tracking, and KPI dashboards

• Lead 100-day integration planning and execution, orchestrating cross-functional teams across all functions

• Track synergy realization against the acquisition thesis; report progress to CEO, board, and the PE sponsor

• Manage cultural integration and senior talent retention through transition periods

Recommended Minimum Qualifications

• Minimum of 10 years of professional experience, with progressive responsibility in senior operating, strategy, or corporate-development roles

• Background in business process outsourcing industry, IT managed services, or a related services/outsourcing environment required

• Corporate development experience: M&A pipeline, diligence, or post-acquisition integration

• Large-scale program and change-management experience with distributed, global teams

• Strong strategic thinker with grounding in valuation dynamics and PE value-creation planning

• Experience partnering directly with a CEO or senior executive in a chief of staff, business operations, or similar leadership capacity

Preferred Skills & Attributes

• Experience operating in a PE-backed environment, with familiarity presenting to boards and investors

• Comfortable with ambiguity and a fast pace, with a build mentality rather than reliance on an existing playbook

• AI-fluent and curious

• Comfortable operating as an enabler to the CEO and a strong leadership team, gently facilitating execution rather than exerting direct authority

• Candid, collaborative working style; builds strong cross-functional relationships

Compensation Range

Base and bonus: $225-250K base + 20% bonus + potential equity. Competitive benefits available.

What to Expect from Our Selection Process

The process includes:

1. CSA Talent Predictive Index Behavioral Assessment

2. CSA Talent 2 step Screening process

3. Virtual Interview with PE Sponsor team

4. Virtual Interview with CEO

5. Virtual Interview with Executive Team Members

6. Case Study

7. Final in-person with CEO

*Note: The Chief of Staff Association partners with The Predictive Index to align workstyles with the role. All applicants complete this quick, two-question, five-minute assessment—no right or wrong answers—and receive a profile readout.

--> Please take the assessment here as you complete your application.

Our client is committed to creating and maintaining a diverse and inclusive workplace where our employees can thrive and be themselves! We welcome all persons into our community. We embrace the diversity of gender, gender identity or expression, race, color, religious creed, national origin, ancestry, age, physical and mental disabilities, medical condition, genetic characteristic, sexual orientation, marital status, family care or medical leave status, military or veteran status, or perceived membership in any of these groups.