Adaptive Security is a Series B AI cybersecurity company that helps organizations strengthen human defenses against phishing attacks through training and phishing simulation technology.
Following rapid scaling of the business, the requirement for a top of industry General Counsel became paramount in order to meet strategic and commercial demands. The leadership team wanted a lawyer who could operate as a true business partner across the organization while remaining comfortable as the sole legal leader for the foreseeable future. The role required someone who could support commercial transactions, work closely with Product, and embrace AI as a tool to improve efficiency rather than build a larger legal team.
The Search
Adaptive Security came to Kerwin with a need to input a seasoned General Counsel into their business at pace.
The mandate evolved throughout the search. Initially, the company focused on candidates with strong commercial experience. As conversations progressed, the leadership team increasingly gravitated toward candidates who combined commercial and product expertise, recognizing the importance of working closely with both business and technical stakeholders.
The search was conducted nationally. While the company initially prioritized candidates in New York and Los Angeles, it remained open to exceptional talent across the country.
Challenges
The search required identifying candidates with a unique combination of capabilities.
Adaptive needed a lawyer who was comfortable serving as the sole attorney and who genuinely wanted to remain in that role rather than build a legal team. The successful candidate needed to lead commercial negotiations, partner with Product, and support a growing AI cybersecurity business.
Cybersecurity experience was also important. While the industry provided a strong talent pool, the combination of cybersecurity expertise, commercial experience, and product exposure was less common. Many candidates had deep experience in one area but lacked the broader background the company ultimately prioritized.
The role generated significant market interest, which meant careful evaluation and calibration were essential throughout the process.
Our Approach
Kerwin worked closely with Adaptive’s leadership team throughout the search, maintaining regular communication and providing market insight on candidate expectations and compensation.
As the role evolved, Kerwin helped the company refine its ideal profile. While the search began with a focus on commercial lawyers, Kerwin consistently highlighted the value of candidates who could bridge commercial and product matters. Over time, the hiring team increasingly aligned around that profile.
The search moved quickly. Kerwin conducted an intensive outreach effort across the cybersecurity market, screening candidates rapidly and providing detailed candidate assessments to help Adaptive make informed decisions. Weekly meetings and ongoing communication ensured alignment throughout the process and allowed the company to move efficiently when the right candidate emerged.
Results
Kerwin completed the search in approximately two months.
The company hired an industry specialist General Counsel who was currently employed at another cybersecurity company. This demonstrated Kerwin’s ability to locate ‘off the market’ talent. Their new GC brought the combination of cybersecurity, commercial, and product experience that Adaptive was seeking.
They also had prior experience operating as the sole lawyer within a business and was known for embracing AI as a tool to drive efficiency. Their background working alongside engineers and supporting cybersecurity products made them a strong fit for the company’s needs.
Impact
The hire gave Adaptive Security an experienced legal leader capable of owning the company’s legal function while partnering closely with commercial and product teams.
The search also demonstrated the value of a highly collaborative client partnership. Adaptive moved quickly, provided consistent feedback, and remained closely aligned with Kerwin throughout the process. Together, the teams identified and secured a candidate who matched both the technical requirements of the role and the company’s long-term vision for how legal would operate within the business.