Associate Chief of Staff

Job Description

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:

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• Ring (exited) – video doorbell and home security
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• Touchland (exited) – premium personal care brand
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• Chronograph – portfolio monitoring and valuation software for institutional private capital investors
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• Alternative Payments – payments and financial infrastructure for services businesses
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• Mangomint – vertical software for salon and spa management
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• Rebuy – personalization and merchandizing software for e-commerce merchants
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• LedgerWay (exited) – rollup of accounting services firms
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• ArcHouse – vertical software for hospice
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• Crown Affair – premium haircare
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• Halo Top (exited) – one of the largest US ice cream brands
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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

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• Manage a wide variety of ad hoc projects
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• Assist investment team with market research, channel checks, competitive analyses, founder references, and other due diligence
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• Help manage the investment pipeline, including the preparation and distribution of a weekly deal pipeline summary
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• Help prepare materials for internal team meetings and external investor updates
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• Maintain internal databases, including portfolio company valuations
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• Help monitor existing portfolio companies, including interaction with founders
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Skills and Qualifications

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• Hard-working, high integrity, and low ego
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• Independent problem solver with extreme attention to detail
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• Strong work ethic – this is not a 9-to-5 role; it is common to work evenings and a few hours per weekend
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• Comfortable with ambiguity and able to prioritize multiple assignments
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• 1-3 years of experience in strategic consulting, corporate strategy, or a high-growth operating environment
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• Comfort with public speaking and cold calling
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• High level of maturity and discretion for confidential information
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• Very well-organized, conscientious, and detail-oriented
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• Exceptional with Microsoft PowerPoint or Google Slides and presentations
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• Comfort with Microsoft Excel and analysis
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• Exceptional written and verbal communication skills
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• Strong hands-on skills developing processes and applications in Claude or other AI tools
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What Sidekick offers

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• Exposure to every part of the venture business: fund finance and operations, investing, portfolio work, and LP reporting
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• Meaningful responsibility and ownership
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• Competitive salary and benefits
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• A small team that moves quickly and prosecutes a rigorous approach to investing
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How to apply

Please send your resume to hr[at]sidekickpartners.com with the subject line “Associate Chief of Staff Candidate – [Your Name].”