Progressly

Nick Candito stumbled into tech almost by accident. A finance major from the East Coast, he joined a small software team in Central Massachusetts building CRM solutions for the pharmaceutical clinical trials industry. That early exposure opened his eyes to the massive inefficiencies lurking inside large enterprises—mountains of paper, Excel spreadsheets, endless email chains. Later, while running operations at Boston-based Crimson Hexagon under CEO Stephanie Newby, he noticed a critical gap: the people who *choose* technologies (executives) have completely different criteria than the people who *use* them (employees). This tension led him to Relate IQ, where he became employee #21 and head of user success. There, he worked alongside founders Steve Laughlin and Adam Evans to build a sales system of engagement that actually fit how people worked day-to-day. When Relate IQ was acquired by Salesforce, Candito not only gained meaningful equity but also learned the playbook for building great enterprises.

In 2014, Candito founded Progressly to solve a problem no existing software addressed: how do Fortune 1000 companies that rely on field workers—energy, utilities, transportation, consumer package goods—actually manage operations across their entire extended value chain? Unlike traditional enterprise software built for desk-bound employees, Progressly adopted a mobile-first strategy targeting people in the field, on job sites, offshore platforms, and remote locations. The company positioned itself as "the operational system of record" to sit alongside CRM (Salesforce), HCM (employee systems), and ERP tools. After some wound-down time at Salesforce, Candito aggressively fundraised starting in early 2015. He and his team deliberately pursued a micro-VC (Initialized Capital, founded by Palantir's Joe Lonsdale) for the seed round plus strategic angels. This approach let him recruit a team of 30 people heavily weighted toward product, design, and engineering—essential for building a complex mobile platform that could integrate with Active Directory, Single Sign-On, and Office 365.

Progressly's go-to-market was decidedly high-touch enterprise. Rather than selling broadly, Candito targeted specific industries where software was desperately needed and where buyers understood ROI. Energy and utilities companies like Chevron became early anchors. Chevron, with 60,000 employees, represented the kind of "whale" account that could define strategy *with* the Progressly team during deployment. Candito noted that "they don't have too many people from Silicon Valley calling into them, but they get the value of technology." His pricing was per-seat SaaS ($19–$49 per user depending on tier) with deployment cycles that stretched months, but conversion rates from pilot to expansion were strong. The first year was modest—north of hundreds of thousands in revenue—but Candito didn't focus on absolute MRR. Instead, he measured pilot-to-expansion conversion and built referenceable customers willing to vouch for him. His CAC payback period was significantly less than 12 months, a remarkable metric for enterprise software.

The enterprise cycle was both blessing and curse. On the surface, slow enterprise sales cycles looked like a weakness. But Candito reframed it: "Some of the largest customers Salesforce has purchased and you're talking nine-figure purchases, and in the deployment, it can take time. But they're defining strategy together." This meant land-and-expand opportunities within massive accounts. His strategy of growing *within* accounts (net positive churn) trumped worrying about logo churn—Chevron alone could represent thousands of additional seats as new use cases came online. The company also explored more flexible pricing models, including Slack-style per-active-user billing rather than seat-based licensing, to better align with value delivered. On the growth front, Candito aimed for 100% year-over-year expansion, but he prioritized having referenceable customers over hitting arbitrary seat targets. His team of 30 included only six people in go-to-market (sales development, account executives, customer success), keeping overhead low while emphasizing product quality and customer intimacy.

By late 2017, Progressly had served hundreds of customers with less than 10,000 total active seats and MRR just under $300K. Candito had raised $10M total and aimed for $5M ARR by December 2017. With advisors like Netscape founder and NetSuite founder Eric Behnke on the cap table, and a clear beachhead in energy and utilities, Progressly was building the "next enterprise company." The key differentiator wasn't speed to value; it was depth. By serving as the operational glue for field-heavy industries where existing enterprise software had failed, Progressly had carved out defensible territory. Candito's playbook—hire great people, target a specific vertical obsessively, measure customer expansion not churn, and build in-market champions—echoed lessons learned at Relate IQ and mirrored the Palantir/Joe Lonsdale DNA embedded in his lead investor.