HacWare CEO On Latest Investment: ‘We Wanted To Understand How To Better Prepare MSPs’

‘The funding went toward researching and developing a software solution called High Risk Monitoring to detect insider threats before they cause a cybersecurity incident,’ says HacWare CEO Tiffany Ricks. ‘What we’ve learned from Northwestern Mutual’s ecosystem is invaluable. We now understand more about the pain points these financial organizations face, particularly the costs and compliance issues tied to human error.’

When cybersecurity startup HacWare began working with MSPs serving financial clients, one thing became clear: human behavior remains the biggest vulnerability in cybersecurity. Now, thanks to an investment from financial services behemoth Northwestern Mutual as part of partaking in the company’s startup accelerator program, the Brooklyn, N.Y.-based vendor is deepening its focus on helping MSPs protect customers in the heavily regulated financial services sector.

CEO Tiffany Ricks said the investment underscores the need for data-driven solutions to combat social engineering and human error. HacWare’s platform uses AI to deliver personalized security awareness training, automate risk detection and generate targeted phishing simulations.

The investment was made through the Northwestern Mutual accelerator program, powered by gener8tor. The 12-month program invests $100,000 in up to 10 companies each per year focused on fintech, insuretech, digital health and data analytics, according to gener8tor’s website.

Ricks said the opportunity with Northwestern Mutual allowed the company to not just receive funding, “but to dive deep into understanding the financial services space and build a product that really meets MSPs’ needs.”

“Our core business is MSPs, and financial services make up about 30 percent of their customer base,” she told CRN. “These firms face stricter compliance regulations and serious fines if they mishandle data. We wanted to understand how to better prepare MSPs to help their clients avoid those risks.”

The partnership came through Northwestern Mutual’s accelerator program, which invests in companies focused on data-driven sustainability which helps businesses improve data privacy, financial resilience and risk management. HacWare’s human-centric approach to cybersecurity fit into that mission.

“The funding went toward researching and developing a software solution called High Risk Monitoring to detect insider threats before they cause a cybersecurity incident,” Ricks said. “What we’ve learned from Northwestern Mutual’s ecosystem is invaluable. We now understand more about the pain points these financial organizations face, particularly the costs and compliance issues tied to human error.”

Unlike endpoint detection or network monitoring tools, HacWare’s high risk monitoring platform focuses on the human factor. The system continuously analyzes user behavior, tracking failed phishing simulations, response times and job roles to flag individuals at greater risk. Once flagged, users are automatically enrolled in more frequent, AI-generated phishing simulations tailored to their industry.

“It’s continuously running in the background,” she said. “If someone repeatedly fails phishing tests or handles sensitive financial transactions, the system identifies them as high-risk. The MSP sees that in their dashboard and can apply escalated training automatically. Once the user completes training and improves their performance, they’re downgraded from high-risk status.”

The AI behind its phishing simulations generates realistic, finance-specific attack scenarios every few days, up from every 21 days for typical users.

Looking ahead, Ricks said HacWare is already developing new tools aimed at unifying cybersecurity and workforce education. The company plans to launch “LMS Plus” in early 2026, an AI-driven learning management system that lets MSPs create both cybersecurity and professional development training content through different prompts.

“Our customers told us they wanted one platform for all types of training,” she said. “With LMS Plus, they’ll be able to build custom content on the fly—security, compliance or new-hire training—all powered by AI.”

HacWare has received a string of investments over the past few years including funding from Google for Startups. The company also raised $2.3 million in a seed round in 2022, according to PitchBook.

Ricks, who said the company is aiming for more funding next year, said the focus remains on tackling the human side of cybersecurity.

“Smart people get hacked all the time,” she said. “Technical teams, support teams—they all need tailored, frequent training. Anyone can be tricked, especially in an age of AI-driven misinformation. Our mission is to make sure MSPs have the tools to stop that from happening.”