Mike Shoss
AI & Product Executive | Scaling B2B SaaS | $150M+ in Fundraising
Updated 9 months ago
20+
Years Experience
16
Roles
20
Skills
2
Education
About
Executive product leader with 15+ years of experience scaling AI-powered SaaS products and securing $150M+ in funding. Expert at aligning stakeholders and cross-functional teams around customer-centric innovation, driving rapid growth and revenue acceleration. Strong communicator skilled in setting strategic vision, building high-impact teams, and achieving measurable results. CAREER HIGHLIGHTS - Secured $150M+ in funding through strategic alignment with investor priorities. - Delivered 105% revenue growth via refined pricing and go-to-market strategies. - Built a global team of 60, driving 400% higher user engagement and doubling conversion rates. - Guided 100+ startups, accelerating market entry, unlocking revenue, and refining product-market fit.
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Experience (16 roles)
Senior Product Manager, New Ventures
CurrentFacilityOS (formerly iLobby) · Permanent Full-time
- Led 0-to-1 launch of ContractorOS, expanding FacilityOS into a multi-sided compliance marketplace. - Established beta-testing, Customer Advisory Board, and validated market through 100+ interviews. - Accelerated time-to-market by 50%; achieved beta in 6 months using Agile and Design Sprints. - Del...
Founder & AI Strategy Principal
CurrentEpilogue is a leading AI consulting firm founded on the belief that businesses deserve more than cookie-cutter solutions. With over 10 years of experience, 3 AI patents, and a proven track record of building innovative products, we’re here to help businesses like yours harness the power of AI to dri...
3 roles · Feb 2021 - Sep 2023
Director of Product Management, Experience Platform & Artificial Intelligence
- Drove product strategy and investment instrumental in securing $150M Series B funding round led by Softbank; regularly briefed executives and board. - Led AI integration initiatives, increasing user engagement 400% and doubling conversions. - Built and scaled 60-member global team across five prod...
Senior Product Manager, Consumer Player & Content Creation
- Scaled content initiatives, growing DAUs 500x; expanded Fortune 500 partnerships. - Pioneered live-shopping experience, boosting conversions 21% and setting the industry standard. Skills: Training · Artificial Intelligence (AI) · Large Language Models (LLM) · Prototyping · Positioning (Marketing) ...
Senior Product Manager, Web Player & Business Portal
- Transitioned platform to self-serve SaaS, growing ARR 10x and enhancing customer acquisition. - Implemented AI playlist optimization, reducing churn 11.4%, enhancing accessibility by 275%. Skills: Training · Artificial Intelligence (AI) · Large Language Models (LLM) · Prototyping · Positioning (Ma...
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Education (2)
Product School
2018 - 2018
Product School’s Product Management course is an 8-week part-time program for professionals with strong technical or business backgrounds who want to transition into product management roles at software-based companies. This is not your traditional lecture class. Expect a healthy mix of group work, hands-on practice with mentors, job search assistance, and an experiential learning process centered around managing the development of software products from beginning to end, and helping you become a product manager. Credential : Mike Shoss Product School
Sheridan College
In Sheridan's Computer Systems Technology – Software Development and Network Engineering program, you'll gain experience with many platforms and environments. Using cutting-edge computer systems technologies (such as Android, iOS and Unity) and industry standards (such as Java, Oracle, C, C# and .NET), you'll learn to create solutions to real-world problems. Software Development & Network Engineering Software Development & Network Engineering | Sheridan Final Capstone Presentation
Skills (20)
Certifications (16)▼
Alexa Development 101
Dabble Lab
Social Marketing
Hootsuite
Segment University
Twilio Segment
Yoast SEO for Wordpress
Yoast
Advanced SEO
Tastic Marketing
Advanced Analytics
Twilio Segment
Entrepreneurship 101
MaRS Discovery District
Python
Kaggle
Segment University - Advanced Products [Protocols]
Twilio Segment
AI for Product Management
Pendo.io
Software Product Management (SPM)
Product School
Sales Academy
Softchoice
Certified ScrumMaster (CSM)
Scrum Alliance
Product Management
Udemy
Pragmatic Marketing Certified
Pragmatic Institute
Segment University - Advanced Products [Personas]
Twilio Segment
Publications (4)▼
Town of Milton fosters creativity and innovation with new collaboration
In Halton · Nov 20, 2023
Seeding Tomorrow: Igniting a Startup Ecosystem in Milton and Halton
LinkedIn · Nov 2, 2023
Turn Your Business Idea Into Reality with the Business Model Canvas
SandboxDMZ · Jul 26, 2017
Milton Innovation Community hosts inaugural meeting
Town of Milton · Nov 16, 2023
Languages (1)▼
Volunteer Experience (19)▼
Founder & President
CurrentShossX
Nov 2023 - Present · 1 yr 8 mos
Mentor - Artificial Intelligence & Product Management
CurrentPlatform Calgary
Mar 2024 - Present · 1 yr 4 mos
Independent Subject Matter Expert
CurrentGLG
Jan 2023 - Present · 2 yrs 6 mos
Mentor - Entrepreneurship Programs
MaRS Discovery District
Jan 2017 - Mar 2018 · 1 yr 3 mos
Independent Subject Matter Expert
CurrentTegus
Jan 2023 - Present · 2 yrs 6 mos
Mentor, Advisor & Speaker
Legal Innovation Zone at Ryerson University
May 2017 - Dec 2019 · 2 yrs 8 mos
Mentor
Treefrog Accelerator
May 2024 - Jun 2024 · 2 mos
Mentor, Advisor & Speaker
The DMZ
Feb 2017 - Oct 2018 · 1 yr 9 mos
Member
Angel One Investor Network
Oct 2023 - Mar 2025 · 1 yr 6 mos
Board Member
CurrentMilton Community Resource Centre
Nov 2024 - Present · 8 mos
Beta Tester
CurrentManus AI
Mar 2025 - Present · 4 mos
Donor
Foldingathome
Apr 2020 - Dec 2023 · 3 yrs 9 mos
Lead Mentor – Artificial Intelligence & Product Management
CurrentThe Forge McMaster
Apr 2024 - Present · 1 yr 3 mos
Advisor
CurrentVarious Startups
Jul 2018 - Present · 7 yrs
Consultant - Artificial Intelligence (AI) Compute
Government of Canada
Jun 2024 - Sep 2024 · 4 mos
Securing Canada's AI advantage: A foundational blueprint Consultation on Artificial Intelligence (AI) Compute
Investor
CurrentAngel Investor
Feb 2021 - Present · 4 yrs 5 mos
Expert-in-Residence – Artificial Intelligence & Product Management
CurrentDMZ
Jan 2025 - Present · 6 mos
My Profile
Treasurer, Board of Directors
Peel Standard Condominium Corporation 910
Apr 2015 - Jul 2019 · 4 yrs 4 mos
Organizer
ProductTank Toronto
Mar 2024 - Jun 2025 · 1 yr 4 mos
ProductTank Toronto Generative AI and Diversity: Transforming Product Management [ProductTank Toronto]
Honors & Awards (17)▼
First Place - Sheridan Capstone Competition [2012]
Issued by Sheridan College · Dec 2012
Associated with Sheridan College Placed first in the Sheridan College Capstone Competition, out of 15 teams. We comprised of a three-person team and made Omega, a 2D platformer game. For more info on our capstone project, refer to the projects section.
Team of the Year - RBC Capital Markets
Issued by RBC · Aug 2012
Associated with RBC Capital Markets
Business Impact Award
Issued by Rogers Communications · Aug 2016
Associated with Rogers Communications Maclean's Education 2.0 View at: https://www.macleans.ca/education-hub/
Customer 1st Award
Issued by Rogers Communications · Aug 2016
Associated with Rogers Communications Maclean's Special Issues
Best Article or Series
Issued by Canadian Online Publishing Awards (COPA) · Nov 2015
Associated with Rogers Communications Best Deals in Real Estate 2015 - MoneySense View at: http://goo.gl/qPr5SN
Best in Business Multimedia
Issued by SABEW Canada · Apr 2016
Associated with Rogers Communications Canada's Best Places to Live in 2015 - MoneySense View at: http://goo.gl/IDiKaY
First Place - Firework Mock Sales Pitch
Issued by Firework · Dec 2021
Associated with Firework The mock pitch consisted of two individual meetings, 30 and 60 minutes respectively, with members from the executive team. The first one being an introduction about who’s is Firework, why to use us and the opportunity for livestream and a short video. The second being Pricing and Technical implementation.
Best Use of Liveshopping [Firework & Who What Wear Bring Video Commerce to OldNavy.com]
Issued by Glossy Fashion Awards · Aug 2023
Associated with Firework The 2023 Glossy Fashion Awards celebrate the industry’s renewed commitment to sustainability, inclusivity and personalized shopping experiences. This year, brands are adopting emerging technology and environmentally-friendly practices as they recognize the importance of creating immersive, sustainable, personalized moments for shoppers.
Best Live Video Strategy [Firework & The Fresh Market – Launch Thanksgiving Video Commerce Campaign]
Issued by Digiday · Mar 2023
Associated with Firework This year’s Digiday Video and TV Awards winners focus on diversity and inclusion, with a greater emphasis on representing marginalized groups and more accurate and respectful depictions of diverse communities in television and film. This group of winners has also increased the production of original content — especially long- and short-form video — to reach Gen Z audiences more effectively. Read More; https://digiday.com/announcement/awards/playstation-and-mocean-pinknews-thesoul-publishing-and-innocean-usa-are-2023-digiday-video-and-tv-award-winners/
Best News Coverage
Issued by Canadian Online Publishing Awards (COPA) · Nov 2015
Associated with Rogers Communications Bearing Witness - Maclean's View at: http://goo.gl/H1SSqP
Best Online Campaign
Issued by Canadian Online Publishing Awards (COPA) · Nov 2015
Associated with Rogers Communications Canada 148 - Maclean's View at: http://goo.gl/UYPQCA
Top 10 PropTech Solution Providers [2019]
Issued by CIO Applications Europe · Aug 2019
Associated with GryphTech In August 2019, PropTech Solutions Inc., the holding company of GryphTech and Phoenix Software, was recognized as a Top 10 PropTech Solution Provider by CIO Applications Europe and was featured as the cover story in the PropTech Special Edition Magazine. Certificate: http://bit.ly/31Z0ESS
Team of the Year Award
Issued by Rogers Communications · Dec 2016
Associated with Rogers Communications Maclean’s Historical Digitization Project
Best Use Of Social Media
Issued by Canadian Online Publishing Awards (COPA) · Nov 2015
Associated with Rogers Communications Canada 148 - Maclean's VIew at: http://goo.gl/UYPQCA
Best in Business Multimedia
Issued by SABEW Canada · Apr 2015
Associated with Rogers Communications Canada's Best Places to Live in 2014 - MoneySense
Chemistry Honors
Issued by Meadowvale Seconday School · Jan 2009
Graduated with the highest mark, 93%, out of all the Grade 12 Chemistry classes, corse code SCH4U.
Business Excellence Award
Issued by Rogers Communications · Aug 2016
Associated with Rogers Communications Maclean's Archive
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