Chief of Staff

Weekday AI (YC W21); Bengaluru; On-site; INR 4,000,000 - 6,000,000; Full time

Job summary

Weekday AI seeks a senior Chief of Staff to partner with the Founder on strategic priorities and high-impact initiatives in Bengaluru. You will translate priorities into structured plans, engage with investors and senior operators, and own cross-functional projects.

The role blends strategy, execution, business development, and relationship building; you will drive initiatives independently, thrive in a fast-paced startup, and represent the Founder in select meetings.

Qualifications

• 8-12 years in strategy, consulting, business development, entrepreneurship, or related roles
• Experience in Sales / Business Development with a track record of building relationships and driving outcomes
• Experience in high-growth startups, entrepreneurial environments, or strategic roles
• Strong strategic thinking, analytical, and problem solving capabilities
• Ability to operate independently with high ownership and limited supervision
• Excellent communication, presentation, stakeholder management, and relationship-building skills

Responsibilities

• Work closely with the Founder on strategic priorities, business initiatives, and critical organizational projects
• Translate high-level business objectives into structured plans, actionable initiatives, and measurable outcomes
• Conduct market, competitive, and business analysis to support strategic decision-making
• Identify and evaluate new business opportunities, partnerships, and growth initiatives
• Support sales and business development efforts, including relationship building, prospecting, and strategic conversations
• Build and maintain relationships with founders, investors, operators, partners, and other key stakeholders
• Prepare strategic presentations, business plans, analysis, and executive-level reports
• Drive cross-functional initiatives from ideation through execution while ensuring timelines and outcomes are met
• Act as a trusted thought partner to the Founder on strategic and operational matters
• Identify bottlenecks, develop solutions, and independently drive high-impact projects
• Represent the Founder and organization in selected external meetings, events, and strategic discussions
• Continuously identify opportunities to improve business processes, growth, and organizational effectiveness

Skills

Strategic thinking

Analytical skills

Problem solving

Relationship building

Stakeholder management

Communication

Presentation skills

Independent ownership

Education

Bachelor's/Master's degree

MBA advantageous

Job description

This role is for one of the Weekday's clients

Min Experience: 8+ years

Location: Bengaluru, Karnataka, India

JobType: full-time

This is not a typical Chief of Staff role. You will work closely with the Founder on high-priority strategic and business initiatives, with significant exposure to investors, founders, senior operators, and a high-quality business network.

The role sits at the intersection of strategy, execution, business development, and relationship building. You will have a high degree of ownership and will be expected to independently drive initiatives, solve complex business problems, and help translate strategic priorities into measurable outcomes.

This opportunity is ideal for someone who thrives in fast-paced environments, enjoys working closely with senior leadership, and is comfortable moving between strategic thinking and hands‑on execution.

Requirements

Key Responsibilities

• Work closely with the Founder on strategic priorities, business initiatives, and critical organizational projects
• Translate high-level business objectives into structured plans, actionable initiatives, and measurable outcomes
• Conduct market, competitive, and business analysis to support strategic decision-making
• Identify and evaluate new business opportunities, partnerships, and growth initiatives
• Support sales and business development efforts, including relationship building, prospecting, and strategic conversations
• Build and maintain relationships with founders, investors, operators, partners, and other key stakeholders
• Prepare strategic presentations, business plans, analysis, and executive-level reports
• Drive cross-functional initiatives from ideation through execution while ensuring timelines and outcomes are met
• Act as a trusted thought partner to the Founder on strategic and operational matters
• Identify bottlenecks, develop solutions, and independently drive high-impact projects
• Represent the Founder and organization in selected external meetings, events, and strategic discussions
• Continuously identify opportunities to improve business processes, growth, and organizational effectiveness

Requirements

Must-Have Skills

• 8-12 years of professional experience in strategy, consulting, business development, entrepreneurship, or related roles
• Experience in Sales / Business Development with a demonstrated ability to build relationships and drive outcomes
• Experience working in high-growth startups, entrepreneurial environments, or strategic roles
• Strong strategic thinking, analytical, and problem-solving capabilities
• Ability to operate independently with high ownership and limited supervision
• Excellent communication, presentation, stakeholder management, and relationship-building skills
• Proven ability to manage multiple high-priority initiatives simultaneously

Good-to-Have Skills

• Strategy or management consulting experience
• MBB consulting experience
• Experience working closely with founders, CXOs, investors, or senior executives
• Previous founder, co-founder, or entrepreneurial experience
• Experience in venture capital, startups, technology, or high-growth businesses
• Strong network across founders, investors, operators, or the broader startup ecosystem

Educational Qualifications

• Bachelor's or Master's degree from a Tier-1 academic institution
• MBA or equivalent qualification from a leading institution is an advantage
• Candidates with exceptional entrepreneurial or professional experience may also be considered

Ideal Candidate Profile

The ideal candidate is a high-agency professional who combines strategic thinking with strong execution ability. You should be comfortable operating in ambiguous situations, taking ownership of problems without waiting for detailed instructions, and interacting confidently with senior stakeholders.

You should enjoy building relationships, identifying opportunities, solving complex problems, and working closely with a Founder on initiatives that can have a meaningful impact on the organization.

Success in the Role

Success will be measured by the ability to independently drive strategic initiatives, strengthen business development and relationship-building efforts, support high-quality decision-making, and consistently convert the Founder's priorities into tangible business outcomes.

This role offers significant exposure to investors, founders, operators, and senior business leaders, along with the opportunity to play a meaningful role in shaping and executing the organization's growth strategy.