Associate Chief of Staff

Firm Overview Sidekick is an early-stage investment firm with offices in New York City and Dallas-Fort Worth. Since 2013, we have backed more than 100 companies across technology, consumer, and business services, investing primarily at the Pre-Seed through Series A stages. We are generalists by design. We underwrite businesses and founders, not technology cycles. Our focus on business model, unit economics, and team have produced industry-leading returns across all prior fund vintages. Portfolio companies include: Ring (exited) – video doorbell and home security Touchland (exited) – premium personal care brand Chronograph – portfolio monitoring and valuation software for institutional private capital investors Alternative Payments – payments and financial infrastructure for services businesses Mangomint – vertical software for salon and spa management Rebuy – personalization and merchandizing software for e-commerce merchants LedgerWay (exited) – rollup of accounting services firms ArcHouse – vertical software for hospice Crown Affair – premium haircare Halo Top (exited) – one of the largest US ice cream brands Job Description Sidekick is seeking a full-time Associate Chief of Staff. This is a unique opportunity to gain exposure to all aspects of company management, venture capital, investment decisions, portfolio company support, and other fund-related activities. The Associate Chief of Staff will be a utility player who owns workstreams across the operational, business development, and investment support teams. We are a small team, so you will be trusted with significant responsibilities early and will manage a broad mix of recurring processes and ad hoc projects. The position will be based in Dallas-Fort Worth or New York City, and it will be in-office at least 3 days per week. Responsibilities Manage a wide variety of ad hoc projects Assist investment team with market research, channel checks, competitive analyses, founder references, and other due diligence Help manage the investment pipeline, including the preparation and distribution of a weekly deal pipeline summary Help prepare materials for internal team meetings and external investor updates Maintain internal databases, including portfolio company valuations Help monitor existing portfolio companies, including interaction with founders Skills and Qualifications Hard-working, high integrity, and low ego Independent problem solver with extreme attention to detail Strong work ethic – this is not a 9-to-5 role; it is common to work evenings and a few hours per weekend Comfortable with ambiguity and able to prioritize multiple assignments 1-3 years of experience in strategic consulting, corporate strategy, or a high-growth operating environment Comfort with public speaking and cold calling High level of maturity and discretion for confidential information Very well-organized, conscientious, and detail-oriented Exceptional with Microsoft PowerPoint or Google Slides and presentations Comfort with Microsoft Excel and analysis Exceptional written and verbal communication skills Strong hands-on skills developing processes and applications in Claude or other AI tools What Sidekick offers Exposure to every part of the venture business: fund finance and operations, investing, portfolio work, and LP reporting Meaningful responsibility and ownership Competitive salary and benefits A small team that moves quickly and prosecutes a rigorous approach to investing How to apply Please send your resume to with the subject line “Associate Chief of Staff Candidate – [Your Name].”