Robert Cicero

Robert is a Partner in PLG’s Corporate and Transactional Practice, advising private and public companies on complex corporate transactions and strategic growth initiatives across the full business lifecycle. He brings more than three decades of experience helping leadership teams, founder-led businesses, entrepreneurs, and private investors as they navigate the ever-expanding opportunities, risks and challenges in today’s fast-moving business environment. Robert is known for his ability to operate as a trusted strategic partner, bringing a pragmatic, solutions-oriented approach, informed by over twenty years of experience in executive in-house roles, most recently as general counsel and chief compliance officer of a publicly traded company, over a decade in private practice in some of the largest and most sophisticated law firms in the world, and stints leading international sales and the human resource function.

Robert’s practice focuses on mergers and acquisitions, raising capital, corporate governance, and commercial contracting, with a particular focus on entity formation and capital structure for early-stage growth companies, representing sellers in private equity rollups, and raising capital through unregistered securities offerings. Robert also serves as outside general counsel to small and mid-market companies, leveraging his broad experience across diverse corporate disciplines, to advise clients on employment and consulting agreements, incentive equity plans, executive compensation, governance arrangements, strategic licensing, and activist and minority stakeholder engagement.

Clients value Robert’s judgment, his “insider” business perspective, and his ability to translate complex legal requirements into clear, actionable guidance that supports strategic business objectives. Robert tries to meet his clients where they are; solving business problems with legally informed business solutions, relentlessly trying to be the outside counsel he would have hired when he was the client, studying and seeking to understand emerging technologies and the impact they have on his clients, and leveraging those technologies to enhance his own practice for his clients’ benefit.

Representative Experience

• Represent founder group in roll up of real estate brokerages in the United States and Canada, for eventual IPO or other exit transaction at +$200MM valuation. Created holding company structure, including management, technology, and operating subsidiaries to facilitate rollup, raised capital through private placement to fund acquisitions, and negotiated initial $10MM acquisition of intellectual property and other assets.
• Represent medical technology startup in opening ninety brain imaging centers across the United States, including raising capital through private placements with a total post-money valuation of +$100MM. Act as outside general counsel, advising on capital structure, corporate governance, employment matters, technology licenses, consulting agreements, and vendor and other service agreements.
• Advise medical technology startup developing online marketplace, including raising capital through private placements with a post-money valuation of +$50MM. Act as outside general counsel, advising on capital structure, corporate governance, incentive equity grants, employment matters, confidentiality and intellectual property protection, consulting agreements, online terms and conditions, and service agreements.
• Renegotiated $100MM credit agreement, including term loan and revolver, for publicly traded consumer products company.
• Took aerospace engineering client public in $50MM IPO, drafting and negotiating registration statement, underwriter agreement, lock up agreement, warrants, employment agreements, equity plan, NYSE listing arrangements, and related documents for the offering, and implementing public company governance protocols and internal controls.
• Represented VR/AR software developer in raising $40MM in seed capital from multiple investors, including direct investment by a London-based family office, and private equity investment via a token subscription facility and related warrants, which required negotiating listing agreements for utility tokens on various crypto exchanges and trading platforms.
• Represented founder of electrical contractor business in the construction industry in $38MM sale of assets to private equity buyer, which included significant rollover equity in acquisition company, and where founder continued to lead the combined entity after the sale.
• Represented accounting firm in $35MM sale of assets to private equity buyer, and subsequent integration into national accounting platform, which included significant rollover equity in acquisition company.
• Renegotiated $30MM credit agreement, including term loan and revolver, for manufacturing company. Act as outside general counsel, advising on commercial agreements, leases, vendor agreements, and employment matters.
• Represented developer of cloud-based software for temporary auto registrations and electronic lien filings in $20MM sale of company to a strategic buyer.
• Represented tree maintenance company in $8MM sale of assets to private equity buyer, which included significant rollover equity in acquisition company.
• Assisted real estate development fund as lead investor in raising $8MM in a private placement for commercial real estate development projects, including forming legal entities, developing capital structure and drafting governance documents and agreements.
• Represented client in exchanging $5MM in senior secured debt, purchased in default from lender, for a majority preferred stock equity position and control of the board of directors, negotiating all documents including charter, bylaws and stockholder agreement.
• Negotiated $2MM private party loan to raise seed capital for early-stage tech startup in the transportation sector.
• Represented investor in $2MM investment in new automotive dealership and adjacent land, negotiating operating agreements, including management rights and buy/sell arrangement.
• Advised private investor in preferred stock investments in pre-IPO private equity portfolio companies, negotiating rights agreements, anti-dilution protections and management rights, among others.
• Advised private investor in purchasing equity investments in private equity-owned pediatric medical practices.
• Represented early-stage automotive consulting services company in negotiating development services agreement, to identify and acquire targets in the automotive and automotive services industries. Act as outside general counsel, advising on master services and various other commercial agreements, employee issues, consulting arrangements, restrictive covenants, and tuck in acquisitions.
• Negotiated separation agreement for Chief Financial Officer of a publicly traded employer, and employment agreement, including equity compensation arrangements, with new employer.
• Negotiated employment agreement, equity compensation arrangements, restrictive covenants and related matters for incoming executive officer of soon to IPO company.
• Negotiated succession plan between founder and minority partner of private equity firm, including buy/sell arrangements, and drafting amendments to governing documents for general partner and related investment funds.