A Crew on a Mission:
We diligently prepare companies to access capital.
We are a team of venture capitalists, financial analysts, technologists, entrepreneurs, CPAs, CAs, CFAs, CBVs, MBAs, dreamers, doers, and trailblazers with a common goal of helping great ideas and smart companies build momentum, create value, and reach new heights.
OUR WHY
Success favours the most diligently prepared.
We saw a gap in the market for start-ups and early-stage companies. These companies often have great potential to realize their vision but struggle to access and communicate with investors. Our programs provide a structured approach with hands-on support and guidance for founders, allowing them to focus on running their business. Meanwhile, investors benefit from our thorough vetting process, giving them confidence in any venture featured on our site.
22
ventures have completed FlightPlan™
14
ventures have proceeded to raise capital with Tailwind
$370
million in total funds raised for Tailwind clients since 2022
85%
of ventures successfully secured capital with Tailwind
Our Crew
Darren Engels, CPA CA, CFA
Chief Engagement Officer
Dreamer, Leader & Adventure Seeker
Darren has over 20 years of business development, strategy, financial and investment experience in a variety of industries and technologies, with a focus on early-stage growth companies. Prior to starting Tailwind in 2018, he worked for a prominent investment bank, where he gained significant knowledge and connections that are now being utilized with Tailwind’s client companies. He holds a Chartered Accountant and a Chartered Financial Analyst designation. Darren finds happiness on two wheels, and while being a professional cyclist is no longer in the cards, he does hope to complete many bike adventures across the world with his two daughters.
Spencer Gunning, CBV
Vice President
Captain of Scaling Strategy
Spencer brings extensive background in banking, corporate development, and investor relations to provide value to Tailwind’s portfolio companies, with a strong foundation in financial analysis, deal structuring, and strategic planning. Before coming to Tailwind, Spencer spearheaded corporate development and investor relations initiatives for a TSX-listed company and worked at a reputable Western Canadian bank in both leveraged debt finance and investment banking roles. Holding a Chartered Business Valuator designation, Spencer provides a distinct perspective on business valuation for Tailwind's companies. Outside of work, Spencer finds himself hitting the links, tending the hockey net, or organizing games of spikeball with friends at Prince's Island Park.
Jenny McLean, MA
Chief Marketing Officer
Marketing Maverick
Jenny drives Tailwind’s growth initiatives and leads the development of the firm’s digital platform. She brings 15+ years of experience in marketing, strategy, and product development, empowering entrepreneurial companies to create impact and value. Prior to joining Tailwind, Jenny led strategic marketing and communications for the research & innovation enterprise at a top five Canadian university, where she was responsible for delivering complex and high-profile projects, enabling research-driven startups to commercialize, and elevating research impacts and innovation outcomes through storytelling, marketing, and engagement.
Andrea Engels
Human Resources
Crew & Culture Champion
Andrea takes care of our growing Tailwind crew, ensuring that Tailwind is the best place to work. When not supporting our thriving crew, Andrea is a dedicated Mom, managing a busy household of two active teenage daughters and two dogs with her husband, Darren. Andrea is clearly the person who keeps it all together, for which Darren is forever grateful. Andrea loves home design, cooking and spending time in sunny vacation spots with her family.
Raj Chitroda
Associate
Vibe Checker for Venture Deals
Raj has experience in venture capital and venture development, across various sectors and stages. Prior to joining Tailwind, he invested in startups at Western Canada’s first university-based venture capital fund and advised scaleups at the Canadian office of a prominent global venture development organization. Raj leverages his background, analytical skills, and passion for the intersection of business and technology to help Tailwind's clients reduce risk and raise capital. In his spare time, he enjoys travelling, watching films, reading, and following NBA basketball.
Lisa Weir, CPA CA
Controller
Commodore of Finance & Controls
With over 12 years of diverse experience in accountancy, advisory, risk management, and controls across a wide range of industries, Lisa brings a wealth of knowledge to the table. Before joining Tailwind, she played a pivotal role in guiding multiple startups through their exciting growth phases. Her journey also includes valuable experience in accounting firms and corporate internal audit, equipping her with a robust skill set. When she’s not crunching numbers or strategizing for success, Lisa indulges her creative side through ceramic arts and creative writing, making her a well-rounded professional with a passion for both precision and artistry.
Raffay Illyas, MSc
Analyst
Raffay brings experience in both life sciences and venture capital, with a focus on seed and Series A startups across North America. Prior to joining Tailwind Ventures, he served as a fund manager at Western Canada’s first university-based venture capital fund, where he attended industry events, sourced deals, met with founders, and led due diligence efforts. He leverages his background in research, quantitative analysis, and a passion for strengthening North America’s startup ecosystem to help Tailwind’s clients reduce risk and raise capital. In his spare time, Raffay enjoys reading biographies, strength training, and discovering new food spots around Calgary
Meet Our Aviators
Our Aviators are a group of experienced entrepreneurs, business executives, venture capitalists, and angel investors who have joined our PaperPlane Projects stream to mentor and guide the next generation of founders.
Neeraj Gupta
Serial Entrepreneur | Investor
Jamie Ha
Executive | CFO | Fintech
Kevin Lo
Executive | Technology | Finance | Investor
Melanie McClare
Entrepreneurial Mindfulness | Start-Up Lover
Martin Molyneaux
Finance | Strategy | Advisor | Investor
Raj Singh
Founder | CEO
Dream big
Our Values
The Tailwind Way
We exist to empower people to build great companies, because we believe economic prosperity uplifts humanity. We challenge the status quo by developing our clients’ competencies to ensure they’re trustworthy – and therefore investable; enabling them to grow and achieve their purpose.
Embody Honour. Live honourably with impeccable words and actions that nurture trust with each other, our clients, investors, and community.
Create Happiness. Create the conditions for happiness – the fuel for a thriving life full of optimism, high-performance, and a life of abundance.
Think Bigger. Commit to a curious, growth mindset and innovative spirit to create meaningful impact, shaping a better world that uplifts humanity.
Exemplify Tenacity. Demonstrate unwavering determination and dedication to transform challenges into opportunities and goals into meaningful achievements.
Ignite Delight. Through intentional design and flawless execution, we craft delightful experiences that exceed expectations, ensuring every interaction is meaningful, memorable, and inspiring.
Want to join our Crew?
We’re always on the lookout for smart, passionate people. If this is you, send us your resume and we’ll take a look!