Jake Cassaday

CEO @ ALT Sports Data

📍 Greater Toronto Area Metropolitan Area, Canada🔄 Updated September 2026💼 9 investments📅 10 years investing🗓 Last invested Oct 2019
VC🌍 Canada
9
Total investments
4
Early stage
4
Mid stage
1
Late stage
10y
Years active

Portfolio

9 investments · sorted by recency
All investments
Early stage
Mid stage
Late stage
Board Member
Oct 2019
Playmaker (TSX-V:PMKR) is a digital sports media company that lives at the intersection of sports, betting, media and technology. Playmaker’s lineup of premier sports media and technology brands is curated to deliver highly engaged audiences of sports fans to sports betting companies, leagues, teams and advertisers.
Board Observer
May 2019
Where parents can safely and sustainability circulate baby & kid items they love. Cause theres always good to go round. We’re reinventing how parents shop for their children by reducing consumerism and saving families time and money. Shop online for brand name, quality checked, secondhand and open box gear with nationwide shipping. To earn money back on gently used gear, sellers can sign up for our convenient, contactless pickup and drop off services.
Board Observer
Nov 2018
Blue J is the leading AI-powered tax research solution, delivering defensible tax answers in seconds—all backed by a rigorously curated content library. Founded in 2015, Blue J is trusted by thousands of organizations, including Big Four firms and Fortune 100 companies. With over 8 million tax questions answered to date, Blue J empowers tax professionals to spend less time researching and more time applying their judgment where it matters most.
Board Member
Oct 2018
Lane is the world’s leading workplace experience platform. Founded in 2014 to transform and connect the workplace, our no-code enterprise software streamlines all aspects of day-to-day office life—from room bookings and access management, to communications and commerce, to events, data, and beyond. Our award-winning mobile and web technology is built to scale, allowing workplace providers to deploy globally and configure locally. Powering 300+ properties across 22 major cities in 8 countries, Lane clients include Brookfield, Oxford, Colliers, Dream, Nuveen, Studio by Tishman Speyer, and more. Putting all of the pieces together, Lane turns any workplace into a place that works. www.joinlane.com www.twitter.com/joinlane www.instagram.com/join_lane
Board Member
Aug 2018
Kira Talent is the world’s only holistic admissions solution designed for higher education. Kira transforms the admissions process by combining on-demand, timed video and timed written assessments with existing admissions requirements. Kira works with over 600 programs worldwide to build applicant-first assessments that identify and select their best-fit students. Kira enhances the existing application by integrating effective, efficient, and fair digital assessments into your school’s existing systems to create a more streamlined admissions process. Working at Kira: At Kira, we are solving complex problems in higher education by building elegant products that are easy to use. We’re a lean, highly-collaborative team who take on big challenges and work quickly and cross-functionally to achieve success for schools and applicants. If you’re an entrepreneurial, startup type, you’re gonna love it here. At Kira, we strive to remain an open, honest, and fun place to work that is shaped by the people within it. We are committed to building and supporting talent that reflects our diverse culture.
Board Member
Aug 2018
We empower entrepreneurs who are rethinking real estate.
early stageReal Estate
Board Observer
May 2017
Circle envisions a world where families can set healthy limits, find balance, and build lifelong habits to get the best out of their digital experiences, rather than being consumed by them. Today, Circle is a category leader in online screen time management and digital parental controls. Our flagship product, Circle Home Plus, is the most comprehensive solution to manage content and time online for Wi-Fi devices at-home and mobile devices across all networks. Circle software is also available through subscription on NETGEAR™ routers. Circle was acquired in December, 2021 by Aura, a leading provider of proactive, all-in-one digital security for consumers, allowing the two companies to join forces to keep families safe online. Aura is a mission-driven technology company dedicated to creating a safer internet for everyone.
Board Member
Dec 2016
At Mainstay, we believe one conversation can spark a brighter future. Our Engagement Platform makes it easy for colleges and businesses to start and measure conversations that drive action at scale. From our rigorous research methods to our Behavioral Intelligence framework — everything we do is designed to help people take the next step toward achieving their goals.
Board Observer
May 2016
7shifts is an all-in-one restaurant team management platform that helps operators: 1) Make more profitable decisions. Youll get the insights you need to make the best team and operating decisions every day. Hit your labor targets with schedule enforcement, optimal labor tracking, and real-time reporting. 2) Improve operating efficiency. Well help get your operations in order and cut down on easy-to-avoid mistakes. Proactively manage compliance, run payroll with ease, and track tasks with digital checklists. 3) Get time back. With all that improved efficiency, youll have more free time to spend on creating great guest experiences. Easier scheduling, centralized communication, and automated tip calculations are at your fingertips. 4) Improve team retention. Youll gain access to the tools you need to help build strong teams. Keep a pulse on team engagement, sentiment, and satisfaction to reduce turnover by 13%. Here’s how your restaurant can benefit from 7shifts: - Save up to 4 hours per week creating and managing your staff schedules - Reduce time spent on scheduling by 80% - Save up to $250 per month in managers time - Reduce labor costs to save up to $3,000 annually - Reduce calls and texts from staff by 70% - Create schedules with 95% labor accuracy - Forecast your future sales with 95% accuracy - Save $1,000s per month in reduced labor costs from more efficient schedule - Save $1,000’s per month in early clock ins and labor overages Its never been easier to manage your teams work schedules, time clocking, team communication, labor compliance, payroll, tips and more, all from one single place. 7shifts can be found in restaurants of all sizes—from mom-and-pop shops to national chains like Bareburger, Highway 55, and Five Guys. Join the 1,000,000+ restaurant pros already using 7shifts to simplify their team management.
Experience · 12 entries
All (12)
Investments (9)
Board (9)
2024
CEO - Canada; SVP Strategy/M&A - North America
Mar 2024
Better Collective is a digital sports media group operating a diversified portfolio of digital sports media, sports betting media and esports & gaming communities. We are on a mission to excite sports fans through engaging content and foster passionate communities worldwide. Incorporated in Denmark in 2004, Better Collective remains under the direct management of its founders, Jesper and Christian. Since our inception, we have undergone substantial growth, driven by successful acquisitions to realize our vision of becoming the leading digital sports media group. Headquartered in Copenhagen, Denmark, and dual listed on Nasdaq in Stockholm and Copenhagen, Better Collective operates globally and + 1,500 colleagues. At its core, Better Collective covers a vast range of sports that spans from the most popular leagues such as the Premier League and NFL to niche competitions. With our media brands, fans can explore the exciting world of sports through various content formats such as exclusive videos, engaging podcasts, editorial sports news as well as expert insights and tips into the latest and upcoming sports events. Our wide range of content engages a sports audience of more than 450 million visits each month across our portfolio of national and international sports media brands. These brands include HLTV, FUTBIN, Action Network, Playmaker HQ, Bolavip, and AceOdds - just to name a few. We have a dream team of highly talented employees with a unique set of digital capabilities and a strong track record in attracting and driving sports fans to our brands. In combination with engaging content offerings, we are able to build and grow a strong and loyal audience across our brands.
2021
Venture Partner
Jun 2021
Relay Ventures is an early stage venture capital firm that invests in passionate entrepreneurs disrupting and creating new markets through mobile technologies. Unlike other funds, Relay exclusively focuses on software for mobile devices and the connected Internet, creating an unparalleled set of networks and resources that tangibly help founders build world-class companies. With offices in Toronto and Calgary, the firm is active throughout North America. For additional information, visit www.relayventures.com.
2019
Board Member
Oct 2019
Playmaker (TSX-V:PMKR) is a digital sports media company that lives at the intersection of sports, betting, media and technology. Playmaker’s lineup of premier sports media and technology brands is curated to deliver highly engaged audiences of sports fans to sports betting companies, leagues, teams and advertisers.
Board Observer
May 2019
Where parents can safely and sustainability circulate baby & kid items they love. Cause theres always good to go round. We’re reinventing how parents shop for their children by reducing consumerism and saving families time and money. Shop online for brand name, quality checked, secondhand and open box gear with nationwide shipping. To earn money back on gently used gear, sellers can sign up for our convenient, contactless pickup and drop off services.
2018
Board Observer
Nov 2018
Blue J is the leading AI-powered tax research solution, delivering defensible tax answers in seconds—all backed by a rigorously curated content library. Founded in 2015, Blue J is trusted by thousands of organizations, including Big Four firms and Fortune 100 companies. With over 8 million tax questions answered to date, Blue J empowers tax professionals to spend less time researching and more time applying their judgment where it matters most.
Show all 12 entries ↓
Investment activity
2016–2019 · 9 investments
20162201712018420192
Recent (last 2 years)Earlier