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