Associate Chief of Staff

Firm OverviewSidekick 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.

Are you the right applicant for this opportunity Find out by reading through the role overview below.
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 securityTouchland (exited) – premium personal care brandChronograph – portfolio monitoring and valuation software for institutional private capital investors Alternative Payments – payments and financial infrastructure for services businessesMangomint – vertical software for salon and spa management Rebuy – personalization and merchandizing software for e-commerce merchantsLedgerWay (exited) – rollup of accounting services firms ArcHouse – vertical software for hospiceCrown Affair – premium haircare Halo Top (exited) – one of the largest US ice cream brands
Job DescriptionSidekick 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.
ResponsibilitiesManage 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 summaryHelp prepare materials for internal team meetings and external investor updatesMaintain internal databases, including portfolio company valuationsHelp monitor existing portfolio companies, including interaction with founders
Skills and QualificationsHard-working, high integrity, and low egoIndependent problem solver with extreme attention to detailStrong work ethic – this is not a 9-to-5 role; it is common to work evenings and a few hours per weekendComfortable with ambiguity and able to prioritize multiple assignments1-3 years of experience in strategic consulting, corporate strategy, or a high-growth operating environment xzbcwsv Comfort with public speaking and cold callingHigh level of maturity and discretion for confidential informationVery well-organized, conscientious, and detail-oriented Exceptional with Microsoft PowerPoint or Google Slides and presentationsComfort with Microsoft Excel and analysisExceptional written and verbal communication skillsStrong hands-on skills developing processes and applications in Claude or other AI tools
What Sidekick offersExposure to every part of the venture business: fund finance and operations, investing, portfolio work, and LP reportingMeaningful responsibility and ownershipCompetitive salary and benefits A small team that moves quickly and prosecutes a rigorous approach to investing
How to applyPlease send your resume to hr[at] with the subject line “Associate Chief of Staff Candidate – [Your Name].”