Errol Apostolopoulos — CEO

A senior executive product leader specializing in SaaS B2B & B2B2C solutions and AI commercialization, with over two decades guiding products from vision to market success. Throughout my career, I’ve consistently delivered innovative, user-centered technology that transforms workflows and drives measurable business value. Agentic AI (2022-2025): At Case IQ, led the vision and execution of generative AI and agentic copilots—AI-powered assistants automating complex tasks, proactively managing workflows, and providing summarizations, significantly enhancing productivity and reducing manual efforts by 30-50%. This enabled substantial growth opportunities across HR, compliance, ethics, fraud, and security markets. AI/ML Analytics & Data (2021-2022): At Appriss Insights, led product strategy and execution across a $150M portfolio of B2C apps, B2B SaaS platforms, and API-driven data solutions. Our products provided people-based risk intelligence supporting critical public safety, fraud prevention, and employment screening workflows. Upon Appriss’s $1.82B acquisition by Equifax, played a key role in the integration planning into the Equifax stack. Conversational AI (2019-2022): At Interactions LLC, oversaw a $120M ARR conversational AI and voice-first portfolio. I drove persona-driven roadmaps and optimized NLU systems, sustaining incremental growth and elevating customer experience. AI/ML Analytics & Insights (2014-2019): At Crimson Hexagon, I transformed a highly technical analytics platform into intuitive, modular products accessible to broader business users. Introducing guided interactions, templated dashboards, and specialized NLP and image-recognition modules, we increased ARR from $10M to over $100M, including merger with Brandwatch and eventual $700M+ strategic acquisition by Cision. Digital- & Mobile-First Transformations (2000-2014): At Razorfish, managed a $30M P&L as GM, pioneering digital-first web solutions for Fortune 2000 fintech and martech brands. Subsequently, at Optaros & Moontoast, I spearheaded early cloud e-commerce and mobile adtech initiatives, including platforms for Walmart.com, Wayfair, RueLaLa, driving substantial revenue growth. My mobile-rich media innovations earned industry recognition, including a Facebook Innovation Award. Over 25 years, my product portfolios have contributed to an IPO (Razorfish), strategic acquisitions (Equifax, Cision), high-profile mergers (Brandwatch), multiple PE-backed acquisitions, and venture exits—demonstrating consistent success in translating emerging technologies into enduring market value.

Stackforce AI infers this person is a SaaS product leader with extensive experience in AI and analytics.

Location: Boston, Massachusetts, United States

Experience: 26 yrs 11 mos

Skills

Product Management
Product Strategy
Generative Ai
Ai/ml Analytics
Conversational Ai
Analytics

Career Highlights

Led successful generative AI product initiatives.
Transformed analytics platforms into user-friendly solutions.
Consistent track record of driving revenue growth.

Work Experience

CPO Copilot

CPO (1 yr)

Case IQ | Formerly i-Sight

SVP Product (2 yrs 6 mos)

Appriss Insights - an Equifax Company

VP of Products (1 yr 3 mos)

Interactions LLC

SVP Product (2 yrs 2 mos)

Brandwatch

Executive Consultant (CX) (1 yr)

Crimson Hexagon

SVP Product (4 yrs)

Spendsetter

SVP Product (3 yrs)

Optaros by MRM//McCann

Head of Innovation and New Products (4 yrs)

Next Place LLC (acquired by private investors)

Founder & CEO (6 yrs)

Razorfish

General Manager (3 yrs)

Sr. Director, Project Management (2 yrs)

Education

Bachelor of Science at Northeastern University

Executive Leadership Program at Harvard Business School

Errol Apostolopoulos

CEO

Boston, Massachusetts, United States26 yrs 11 mos experience

AI EnabledAI ML Practitioner

Key Highlights

Led successful generative AI product initiatives.
Transformed analytics platforms into user-friendly solutions.
Consistent track record of driving revenue growth.

Stackforce AI infers this person is a SaaS product leader with extensive experience in AI and analytics.

Contact

Skills

Core Skills

Product ManagementProduct StrategyGenerative AiAi/ml AnalyticsConversational AiAnalytics

Other Skills

Artificial Intelligence (AI)Business StrategyWorkflow AutomationData SolutionsNLU SystemsCustomer ExperienceNLPGrowth StrategiesE-commerceEntrepreneurshipMobile ApplicationsUser ExperienceSocial Media MarketingAgile MethodologiesMobile Devices

About

Experience

Cpo copilot

CPO

Mar 2025 – Present · 1 yr · Boston, MA · On-site

As a fractional CPO, I partner with executive teams to define and accelerate product strategy, with a specialized focus on AI-powered innovation. My responsibilities typically include shaping and executing roadmaps for AI feature development (e.g., generative AI, NLP/NLU, advanced analytics), aligning cross-functional teams around data-driven product initiatives, and operationalizing AI capabilities into scalable SaaS offerings. I also lead commercialization efforts, guide pricing and packaging strategies for AI products, and support M&A due diligence and integration. My approach blends product leadership, market insight, and technical depth to drive measurable growth and sustainable differentiation.
As an advisor, I help organizations professionalize their product lifecycle management—from initial discovery through delivery and iteration. I provide strategic guidance on implementing structured frameworks for prioritization, roadmap planning, go-to-market alignment, and cross-functional execution. My focus is on enabling scalable processes that improve speed to value, reduce waste, and ensure product investments are consistently aligned with customer needs and business outcomes.

Product ManagementProduct StrategyArtificial Intelligence (AI)Generative AIBusiness Strategy

Case iq | formerly i-sight

SVP Product

Sep 2022 – Mar 2025 · 2 yrs 6 mos · Remote

Private equity-backed. Case IQ is an AI-powered investigative case management solution. Product provides organizations with unrivaled case intake capabilities, workflow configuration, automation, and advanced analytics that are essential for increasing the capacity, accuracy, and efficiency of workplace investigation teams. Leveraging generative AI (Azure OpenAI) technology for case summarization. Responsible for strategic management of the end-to-end product management lifecycle for the entire product portfolio. Create and execute innovative strategies to drive growth, competitive advantage, and financial and operating performance, including M&A diligence and integration activities. Develop product-led growth strategies and operational excellence. Lead team of product managers, data science, project managers, UX designers and operations.

Appriss insights - an equifax company

VP of Products

Apr 2021 – Jul 2022 · 1 yr 3 mos · Remote

Equifax acquired Appriss Insights. AI-powered data products. Responsible for strategic management of the end-to-end product management lifecycle for the $150M+ Insights product portfolio, including SaaS B2C, SaaS B2B, and API-driven data & analytics offerings. Create and execute innovative strategies to drive growth, competitive advantage, and financial and operating performance, including integration of acquisitions. Develop product-led growth strategies and operational excellence. Led team of product managers, data science, project managers, UX designers and operations.

Interactions llc

SVP Product

Jan 2019 – Mar 2021 · 2 yrs 2 mos · Greater Boston Area · Hybrid

Acquired by SoundHound AI. Private equity-backed. Conversational AI (voicebots and chatbots). Interactions builds and delivers cloud-hosted AI-driven Virtual Assistant applications that enable businesses to deliver automated natural language communications for enterprise CX solutions, including voice and digital bots. Led the $100M+ product portfolio for a breadth of offerings, including expanding the portfolio to drive new revenues with SaaS, platform-enabled services, and analytics.

Brandwatch

Executive Consultant (CX)

Jan 2018 – Jan 2019 · 1 yr · Greater Boston Area

Cision acquired Brandwatch. Previously, upon merger (Brandwatch + Crimson Hexagon), reported directly to CEO and helped drive strategic partnerships, alliances and strategy focused on the CX ecosystem including data partnerships. Helped secure, negotiate and expand partnership revenue streams and opportunities.

Crimson hexagon

SVP Product

Jan 2014 – Jan 2018 · 4 yrs · Greater Boston Area · On-site

Brandwatch acquired Crimson Hexagon (private equity and venture backed). AI-powered text and image analytics. As the executive leader of products at Crimson Hexagon, led the growth of an AI-powered consumer analytics SaaS B2B platform portfolio. Expanded product portfolio from single UI-based product to include not only additional UI-based products but also multi-data set API offerings along with automated insights. Customers included global 2000 enterprises, mid-market businesses, agencies, and data partners. Grew to a $100M+ ARR business.

Spendsetter

SVP Product

Jan 2011 – Jan 2014 · 3 yrs · Greater Boston Area · On-site

Spendsetter acquired Moontoast (Venture-backed). Previously, led entire product management lifecycle and team for Moontoast a venture-backed SaaS platform, delivering a social/mobile adtech creative platform for creation and delivery of interactive rich media ad units into social & mobile networks. Customers included global 2000 brands and design agencies. Noteworthy as 1 of only 2 ad units certified by Facebook within their newsfeed prior to their IPO, designated Facebook Innovation Award.

Optaros by mrm//mccann

Head of Innovation and New Products

Jan 2007 – Jan 2011 · 4 yrs · Greater Boston Area

MRM/McCann acquired Optaros. Drove product innovation strategy for PaaS offering delivering innovative social and mobile eCommerce software solutions to leading online digital retailers and brick-and-mortar retailers. Built platform for private-sale eCommerce solution including Rue La La & Wayfair's Joss&Main.

Next place llc (acquired by private investors)

Founder & CEO

Jan 2001 – Jan 2007 · 6 yrs · Greater Boston Area

Acquired by private investors. Founded, led and exited at 3X multiple a venture-backed entertainment/hospitality venture including TV shows, digital media and multiple themed restaurant venues. Owner/operator for unique sports-themed venues with original content creation delivered through online & offline media platforms. Grew P&L and team from 1 to 100+ employees and raised funds, built profitable business and sold successfully.

Razorfish

2 roles

General Manager

Promoted

Jan 1997 – Jan 2000 · 3 yrs · Greater Boston Area · On-site

IPO. P&L leader for $30M+ line of business, technology-enabled services, led a 150-person team delivering digital products, frameworks, and services for F500 clients. Among the first generation of creative digital agencies.