Practice area

Direct Equity

Covenant represents institutional investors in direct and venture investments at every stage, from SAFEs and convertible notes through seed, early-stage, and late-stage priced rounds. The team regularly advises venture capital funds, university endowments, and other investors on new investments, follow-ons, bridge financings, and pay-to-play and other structured rounds.

Why Covenant

On the investor's side

Covenant represents the investor and only the investor, so every review focuses on what matters from that position, including information rights and control concerns.

Every term, benchmarked

Each term is measured against data from the investor's own portfolio as well as the market standard. Alerts flag any departure from terms the investor has accepted before, as well as anything that is off-market.

Efficiency, always

AI makes the process faster, and the resulting time and cost savings are passed on to the client. Issues lists and document drafts are produced with predictability and speed in mind. Those efficiencies are built into the fee from the start.

Pricing predictability

Covenant can always provide a fixed fee and can provide reliable pricing for every round in which the investor is not leading.

Areas we serve

Every direct investment,
fully covered

Preferred Stock

Classic “priced rounds” for venture-backed companies. New series of preferred stock at a negotiated valuation with rights, preferences and privileges. Can be Pre-Seed, Seed, Series A, B, C, and later with a full suite of investment documents.

Series Seed

Lightweight preferred with simpler documents and fewer investor protections, used for smaller early rounds.

Extensions

To add capital on the same or similar terms as a prior round, often without a full new negotiation.

SAFEs

Non-debt that converts into equity at the next priced round.

Convertible Notes

Debt that converts into equity at a qualified financing. Can be used to bridge between priced rounds.

Venture Debt

Senior loans to VC-backed companies, often paired with warrants and used to extend runway between equity rounds.

Bridge Rounds

Interim financings, often through notes or SAFEs from existing investors, that carry a company to its next round.

Pay-to-play Rounds

Penalize existing investors who don't participate, for example by converting their preferred to common.

Down Rounds, Recapitalizations and Cramdowns

Priced below the prior round's valuation, which triggers anti-dilution adjustments or restructures the cap table, often converting preferred to common or resetting preferences.

Structured Equity

Priced rounds with heightened terms, such as participating preferred, multiple liquidation preferences, ratchets, or redemption rights.

Secondary Transactions

To provide liquidity to existing shareholders. No new capital goes into the company.

Your institutional memory

Your portfolio,
in one place

Every investment position lives in the Covenant portfolio view, on the same platform as its fund commitments, building a single source of truth for all portfolio data.

Covenant portfolio analysis view
Lead attorneys

Decades of venture financing experience

Jen Berrent
Jen Berrent
Co-Founder & CEO

Jen founded Covenant to rethink the way legal services are delivered to clients and to give investors the legal intelligence that the traditional model has consistently failed to deliver. Previously, Jen served as COO and CLO of WeWork and was a corporate partner at WilmerHale, where she advised on complex transactions and led the New York emerging company practice.

Herman Cheung
Herman Cheung
Senior Counsel

Herman leads Covenant's direct investments and venture financing practice. Previously practiced at O'Melveny & Myers in corporate finance and credit. Herman has represented a variety of venture funds as well as companies in venture financings, giving him a deep understanding of venture transactions and the players that are involved.

Recent work

Every stage, every structure

Represented an early-stage venture capital firm as lead investor in a $5M Series A financing of an AI-powered customer advocacy platform

Advised family office in a $150M+ Series E financing of a clinical-stage biopharmaceutical company

Advised university endowment in a $40M Series D pay-to-play financing of a pediatric telehealth provider

Advised university endowment in a bridge convertible note financing of a clinical-stage biopharmaceutical company

Advised university endowment in $300M Series H financing of a fuel-cell technology company

Advised late-stage venture investor in Series C financing of technology-focused bank

Represented venture capital fund in Series A financing and concurrent secondary purchase of common stock in a healthcare AI company

Represented an early-stage venture fund in its follow-on investment in a $2.5M bridge convertible note financing of a healthcare AI company

Represented an early-stage venture capital firm in various SAFE investments in several AI and analytics start-ups

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