ABOUT UPSIGHT
We started UpSight because we kept watching the same thing: teams talk to customers, but they're not always reaching the right people or asking the right questions. And whatever they do learn scatters across five tools and someone's memory.
We're building the system that helps you engage the right people, understand what matters, andserve them better.
ENGAGE
Know who to talk to, what to ask, and what you've already learned. Reach the right people on the right topics.
UNDERSTAND
Every insight links to who said it, when, and why it matters. Grounded, not generated. Cross-source, not siloed.
SERVE
Turn what you learn into how you deliver. Build the right thing, close the right deals, retain the right customers.
LEADERSHIP

Founder & CEO
Multi-exit founder, CEO, CPO, and CMO with over two decades building and scaling B2B SaaS companies in cybersecurity, AI, and cloud networking.
As co-founder and CEO of NSS Labs, Rick created an entirely new market category by talking to hundreds of IT security professionals and discovering they were making million-dollar purchasing decisions with zero empirical data. That insight-driven approach to customer discovery has been the through-line of his career.
Rick has held executive roles at ESET, Accuknox, Acalvio, Tempered Networks, and Websense, and is currently building UpSight, an AI-powered customer intelligence platform to help teams get their customer. He is an active startup advisor and investor in the San Diego ecosystem, and a regular speaker on AI, product strategy and go-to-market.
As a Techstars mentor, Rick brings a founder's instinct for finding the real problem behind the stated problem — and helping teams build conviction through evidence, not assumptions.
CAREERS
Small team, real ownership, customers who care. We're hiring people who'd rather ship than deck.
Growth
Own the funnel from first touch to activation. You'll run experiments across content, community, and product-led channels to put UpSight in front of founders and consultants who talk to customers every week.
AI Engineer
Build the synthesis and traceability engine that makes every insight provable. You'll work across LLM pipelines, embedding search, and structured extraction — shipping AI that's useful, not just impressive.
UX Researcher
Practice what we preach. You'll run continuous discovery with our users, surface patterns, and translate evidence into product decisions — using UpSight itself as your primary tool.
Enterprise Sales
Take UpSight into mid-market and enterprise teams who are drowning in unstructured customer signal. Consultative, evidence-driven selling — no scripts, no spam.