Bob Desantis

Board Member, Investor, Advisor, Retired SaaS Operating Executive

📍 Vashon, Washington, United States🔄 Updated September 2026💼 7 investments📅 9 years investing🗓 Last invested Dec 2025𝕏 @upgrade_to_unlock
Angel investor🌍 United StatesInvested this year
7
Total investments
2
Early stage
3
Mid stage
1
Late stage
9y
Years active

Portfolio

7 investments · sorted by recency
All investments
Early stage
Mid stage
Late stage
Investor
Dec 2025
Halosight is AI for account managers and customer advisors who want to use every email, text, ticket, and conversation to prioritize, personalize, automate and coach. Turn customer interactions into profitable team improvements. Halosight is an AI service available on the Salesforce AppExchange. If your team needs to qualify opportunities, improve their performance, or discover what’s working in their playbook, set up a demo today.
Investor & Advisor
Jun 2021
TRIYO enables financial institutions to adopt an AI-first strategy by extracting and structuring hidden work data from legacy systems and human-centric processes. This contextualized data provides the foundation for advanced analytics, LLMs, automated regulatory reporting, and 360° operational visibility. By doing so, TRIYO helps institutions reduce compliance risk, drive significant operational efficiencies, and future-proof their operations with minimal change management.
 Today, TRIYO is already powering critical use cases: automating STR/AML regulatory reporting to FINTRAC, where Credit Unions have achieved over 50% efficiency gains in less than 100 days; and streamlining engineering and resource management processes at a Tier 1 North American bank, eliminating manual reporting decks and surfacing real-time capacity insights. These implementations highlight how the same platform can simultaneously strengthen compliance, improve operations, and accelerate secure AI adoption. Our platform enables the automated reporting of complex processes, delivering a 360-degree view and actionable insights across critical workflows, including off-platform communications. TRIYO also structures contextual work data to power AI adoption — unlocking the potential for automation, predictive analytics, and smarter decision-making
Investor & Advisor
Aug 2020
Spending decades as SaaS operators, we faced first hand the limitations of traditional data architectures. Expensive, bulky, and often failing to answer simple questions, these tools ultimately created more stress than insights… and that’s why we built Discern. Delivered as out of the box business intelligence, Discern breaks down operational siloes, answers key questions, and identifies critical risks. Through partnership with top PE firms, Discern has incorporated best practice dashboards and KPI definitions directly in the platform, making it easy for you to align your business with operational excellence. Because we’ve standardized system integrations, KPI calculations, and GTM dashboards, Discern has the unique advantage of delivering real insights in a matter of weeks. Are you ready to say goodbye to the BI BS?
Board Member
Feb 2020
Provar pairs intuitive testing solutions, including Provar Automation and Provar Manager, with world-class service to help teams capitalize on their Salesforce investment. Its comprehensive suite of testing products creates a quality hub designed to improve release agility, drive down system defects, and advance innovation, meeting people at every stage in their journey — from the individual manual tester to comprehensive QA teams with automated workflows. Visit www.provartesting.com to learn more.
Investor & Board Member
Oct 2018
OwnBackup believes that no company operating in the cloud should ever lose data. With comprehensive backup, visual compare, and fast recovery capabilities, we have helped hundreds of organizations through data loss and corruption crises. Our solution also provides enterprises with the performance and reporting required to meet compliance regulations in a number of industries. We provide secure, automated, daily backups of SaaS and PaaS data, including Salesforce. The company was co-founded by technology veterans with deep experience in data-recovery, data-protection and information-security. OwnBackup’s solutions provide built-in protection against data loss and corruption caused by human error, malicious intent, integration error and rogue applications. All of this has helped make OwnBackup the top-ranked backup and restore ISV on the Salesforce.com AppExchange, a venue the solution has been listed on since 2012, and to gain recognition as a Gartner “Cool Vendor” in Business Continuity and IT Disaster Recovery.
Investor & Board Observer
Aug 2018
Copados platform is built for the unique demands of business applications. We align software development with your core business processes, optimize pre-built solutions, and ensure continuous collaboration. This is DevOps for Business Applications—agile, user-focused software tailored to your enterprise needs. Across the globe, 1,400+ customers and 100,000+ Copado Community members leverage our complete and extensible DevOps solution to scale Salesforce, maximize business value and accelerate their careers.
Investor & Advisor
Jan 2017
Fullcast is the leading AI-native Revenue platform that unifies planning, execution, and performance across go-to-market teams. Through its integrated product suite, Fullcast enables organizations to connect strategy to action and optimize every part of the revenue engine. Fullcast delivers a complete “Plan-to-Pay” platform that drives predictable growth and productivity. Founded with the mission to help companies scale smarter, Fullcast empowers GTM teams to align, automate, and accelerate revenue — all within a single connected ecosystem. We seamlessly connect go-to-market planning activities with tactical sales execution, enabling your operations, sales, finance, marketing, and customer success teams to make continuous adjustments in response to real-time strategy changes. From territory management to commissions and performance tracking, we operate with speed, agility, and AI-powered automation. We have over 10 million users, the backing of top tier venture capital firms (Sequoia, Craft, Wing, Tokyo Black), and an incredible tailwind of AI momentum and enthusiasm.
Experience · 9 entries
All (9)
Investments (7)
Board (3)
2025
Investor
Dec 2025
Halosight is AI for account managers and customer advisors who want to use every email, text, ticket, and conversation to prioritize, personalize, automate and coach. Turn customer interactions into profitable team improvements. Halosight is an AI service available on the Salesforce AppExchange. If your team needs to qualify opportunities, improve their performance, or discover what’s working in their playbook, set up a demo today.
2021
Investor & Advisor
Jun 2021
TRIYO enables financial institutions to adopt an AI-first strategy by extracting and structuring hidden work data from legacy systems and human-centric processes. This contextualized data provides the foundation for advanced analytics, LLMs, automated regulatory reporting, and 360° operational visibility. By doing so, TRIYO helps institutions reduce compliance risk, drive significant operational efficiencies, and future-proof their operations with minimal change management.
 Today, TRIYO is already powering critical use cases: automating STR/AML regulatory reporting to FINTRAC, where Credit Unions have achieved over 50% efficiency gains in less than 100 days; and streamlining engineering and resource management processes at a Tier 1 North American bank, eliminating manual reporting decks and surfacing real-time capacity insights. These implementations highlight how the same platform can simultaneously strengthen compliance, improve operations, and accelerate secure AI adoption. Our platform enables the automated reporting of complex processes, delivering a 360-degree view and actionable insights across critical workflows, including off-platform communications. TRIYO also structures contextual work data to power AI adoption — unlocking the potential for automation, predictive analytics, and smarter decision-making
2020
Rosebriar Consulting
Principal
Aug 2020
Investor & Advisor
Aug 2020
Spending decades as SaaS operators, we faced first hand the limitations of traditional data architectures. Expensive, bulky, and often failing to answer simple questions, these tools ultimately created more stress than insights… and that’s why we built Discern. Delivered as out of the box business intelligence, Discern breaks down operational siloes, answers key questions, and identifies critical risks. Through partnership with top PE firms, Discern has incorporated best practice dashboards and KPI definitions directly in the platform, making it easy for you to align your business with operational excellence. Because we’ve standardized system integrations, KPI calculations, and GTM dashboards, Discern has the unique advantage of delivering real insights in a matter of weeks. Are you ready to say goodbye to the BI BS?
Board Member
Feb 2020
Provar pairs intuitive testing solutions, including Provar Automation and Provar Manager, with world-class service to help teams capitalize on their Salesforce investment. Its comprehensive suite of testing products creates a quality hub designed to improve release agility, drive down system defects, and advance innovation, meeting people at every stage in their journey — from the individual manual tester to comprehensive QA teams with automated workflows. Visit www.provartesting.com to learn more.
Show all 9 entries ↓
Investment activity
2017–2025 · 7 investments
2017120182202022021120251
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