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Shikha Gupta

Founder at 99Yellow

Last Active: 06 April 2026

Job Views:  
1417
Applications:  521
Recruiter Actions:  202

Posted in

Consulting

Job Code

1680468

Chief of Staff

99Yellow.8 - 14 yrs.Bangalore
Posted 3 weeks ago
Posted 3 weeks ago

The Opportunity

Be the CEO's strategic right-hand and the company's operational backbone. You will own execution rigor, priority alignment, cross-functional coordination, and strategic initiatives. You're the person who makes sure the ambitious vision doesn't get lost in the chaos of rapid scaling.

The Challenge

RDA is transforming from a project-centric services company to a product-led platform company. This requires:

- Ruthless prioritization: We have 1000 things to do; which 5 move the needle?

- Cross-functional coordination: Align BD deals with engineering capacity, product strategy with customer needs

- Execution rigor: Turn strategic initiatives into quarterly OKRs and daily work

- Culture of accountability: Ensure every team knows their goals and how they contribute

- Rapid iteration: Learn fast, adjust quickly, scale what works

Key Responsibilities

Strategic Execution (40%)

- Own quarterly planning: Translate CEO vision into OKRs and KPIs for all teams

- Drive board readiness: Prepare quarterly business reviews, financial forecasts, strategic updates

- Lead strategic initiatives: Product transformation, office expansion, vertical entry, partnerships

- Define and track success metrics: Revenue, NPS, attrition, engineering velocity, etc.

- Facilitate quarterly business planning and 12-month roadmap alignment

Operational Coordination (35%)

- Own the org's operating cadence: monthly all-hands, quarterly reviews

- Facilitate cross-functional committees: Deal closure, capacity planning, pod steering

- Manage calendar and bandwidth for CEO (protect focus time)

- Coordinate between CEO, VP Engineering, VP Product, VP Sales/BD

- Track and escalate blockers: Budget, hiring, legal, policy implementation

Initiative Management (15%)

- Own high-impact projects: compliance certifications, brand refresh, etc.

- Project management: Timeline, stakeholders, dependencies, risk mitigation

- Own culture initiatives: Off-sites, team building, communication

- Drive policy implementation: NDAs, onboarding, documentation, processes

Insights & Analysis (10%)

- Maintain strategic dashboard: Revenue, headcount, capacity utilization, NPS, attrition

- Conduct strategic analysis: Market sizing, competitive landscape, partnership opportunities

- Synthesize insights from all teams and present to leadership

- Identify trends, risks, and opportunities early

What We're Looking For

Core Competencies

- 5+ years as Chief of Staff, VP Operations, or equivalent executive role

- Strategic thinking: You can see how disparate pieces fit together; you think systematically

- Execution excellence: You sweat the details while keeping the big picture in view

- Cross-functional fluency: You understand sales, engineering, product, ops, and finance

- Communication: You're clear, concise, and can translate strategy into action

- Relationship building: You have credibility across all teams; people trust and follow you

- Comfort with ambiguity: You operate in early-stage chaos; you create order without rigidity

Proven Track Record

- Scaled a team or organization significantly (10- 50+)

- Experience in operations, strategy, or similar cross-functional leadership

- Track record of driving through OKR-based planning

- Experience in tech/product companies (you understand velocity and iteration)

Culture Fit (Non-Negotiable)

- Mission-driven: You care about the mission, not just the role

- High agency: You own outcomes, take initiative, don't wait for permission

- Intellectual rigor: You ask hard questions, challenge assumptions, dig into data

- Inclusive: You listen to all voices; you're not a yes-man

- Humble: You learn fast, admit mistakes, iterate on your approach

Compensation & Expectations

- Base + Performance Incentives + Equity (significant equity due to leverage)

- 45-50 hour weeks (executive-level workload; on-call for urgent matters)

- Quarterly off-sites, professional development, executive coaching

- Board-level visibility and strategy influence

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Posted by

user_img

Shikha Gupta

Founder at 99Yellow

Last Active: 06 April 2026

Job Views:  
1417
Applications:  521
Recruiter Actions:  202

Posted in

Consulting

Job Code

1680468