A city can have a surprising amount of business knowledge sitting between assignments. The executive has finished one career. The founder has reached a problem she has never seen before. They might live a few kilometres apart and still never meet. Sandi Gilbert has made that gap part of her working life in Calgary, where experience and ambition often need somebody to arrange an introduction.
She is CEO of InterGen and managing partner of InterGen Capital, connecting growing companies with Alberta’s business talent and investment. She also founded DealPoint, software for the practical work of raising private capital. One role brings people together; the other helps their decisions become transactions. Follow the two, and a fairly consistent interest emerges: what prevents a willing person from getting something useful done?
The subject sounds grand until you get to the particulars. An operator who knows how to grow a business. A founder who needs that knowledge. An investor ready to participate. Documents that have to be completed. Gilbert’s career lives among those particulars. The future may arrive wearing a conference badge, but somebody still has to get the paperwork right.
A second act needs an assignment
InterGen’s roots lie in Top 7 Over 70, the awards programme recognising people who launch ventures or initiatives after seventy. Jim Gray and Brian Felesky are listed as InterGen’s founders. Gilbert leads an organisation built around the idea that accumulated business experience can remain useful to the next generation of companies. Retirement, in this arrangement, leaves room for another assignment.
The awards connection gives the work an unusually concrete starting point. Age is usually introduced into a business biography as a deadline or a milestone already passed. Here, it provides evidence that another chapter is possible. InterGen turns that observation towards the needs of growing companies: who has already learned something that a younger business is about to need?
The distinction matters to Gilbert’s story. She works with entrepreneurs moving beyond the start-up phase, when a working product can bring an expanding collection of management decisions. Having started is one achievement. Knowing how to organise the next stage asks for different experience. InterGen’s premise puts people who have spent careers making those decisions within reach of people encountering them for the first time.
Talent, learning and capital: the three parts of InterGen’s stated approach.
In December 2019, the Opportunity Calgary Investment Fund announced up to $100,000 to help InterGen launch a platform matching retired or transitioning local executives with later-stage start-ups. The plan included development support, roundtables and a speaker series. Even at launch, the introduction came with an acknowledgement that a match would need somewhere to go.
That announcement also put knowledge transfer at the centre of the project. A useful connection takes more than two names on a list. The founder needs to recognise the help being offered; the experienced leader needs a problem worth engaging with. Gilbert’s work occupies that space between availability and usefulness, where a city’s business history can become part of a company’s next decision.
Before the introductions, the knocking
Gilbert grew up on a Manitoba farm and came to Calgary interested in finance. She recalls knocking on brokerage doors until she found work at Nesbitt Burns. There she met mentor Stuart Dunn, whose daily habit of collecting jokes helped establish a shared sense of humour. The relationship brought her into a business world she was eager to learn.
There is something pleasingly ordinary about the joke book. A finance career can be recounted entirely through transactions and appointments, yet here is a relationship partly remembered through laughter. Her later work gives that early connection a professional echo: an experienced person has knowledge, a newcomer has questions, and a conversation lets something pass between them.
Her public career subsequently included SeedUps Canada, where she worked on technology linking companies with private investors. An older professional biography describes virtual environments for preparing, presenting and executing capital raises, then managing investors through to an exit. The vocabulary would change as her products developed. The problem of connecting a business with private capital remained.
By 2019, an Alberta Securities Commission speaker biography described her as founder of Crowd Capital, the fintech company behind DealPoint, and chair of the National Angel Capital Organization. It also identified her work leading InterGen Connect. Software, investor communities and business expertise were already appearing together in the same career, rather than waiting for separate chapters.
The paperwork gets a prize
DealPoint’s company history dates its beginnings to 2017 and its pilot to 2018, developed with an exempt market dealer. A venture suite followed in 2020. Its work includes investor onboarding, document execution and investment workflows. These are the tasks behind a capital raise that make the celebratory announcement possible.
For Gilbert, that offers another way to work on access. An introduction can bring an investor to the table; a workable process helps an investment proceed. In a business devoted to new possibilities, the repetitive administrative parts are easy to overlook. DealPoint has made them the product. The attraction is straightforward: less friction between agreeing to participate and completing the transaction.
On October 4, 2023, that work produced a rather photogenic result. DealPoint won the $125,000 first prize in the Digital Commerce Calgary Fintech Awards at Platform Calgary. The money was non-dilutive, so the company could put it to work without exchanging an ownership stake. Gilbert was photographed at the centre of the winners, holding a cheque considerably easier to read than most investment documents.
Her reaction returned quickly to the people building the company. She spoke about what the prize would mean for the team, and about the exposure and workshops they had received through the competition. For someone whose work includes finding experienced help for founders, it was a fitting detail: her own company had benefited from a programme that provided more than money.
“I’m really excited what this means for the team to actually take it to the next level.”
Sandi Gilbert, after DealPoint’s 2023 award
DealPoint’s published 2025 milestone reports more than $1 billion in financial transactions across over 15,000 investors. Those are platform figures, describing the activity supported by the software. They provide a measure of how much investment administration can sit behind a relatively quiet product category.
Who helps after the cheque?
InterGen gives Gilbert a view of what happens around an investment. Its public account of a Wine Wednesday conversation with ZayZoon founders Tate Hackert and Darcy Tuer describes a local fintech company that had grown from a handful of people to more than 120 team members at the time. ZayZoon was also an InterGen Capital portfolio company. The conversation linked growth with the support of Alberta investors.
These events give Gilbert another role: asking questions of people who have lived through the decisions other founders are facing. A business story becomes useful when its details can travel. What did the team need? Who helped? Which decisions changed the options available? A conversation with founders can make experience accessible without requiring everybody in the room to repeat the same mistakes.
At Inventures in May 2024, Gilbert joined James Lochrie of Thin Air Labs and Vincent Ircandia of StellarAlgo for a panel about mentorship and building technology companies in Canada. The discussion’s stated themes included the difficulty of raising scale capital and the cycle created when successful founders begin investing in those following them. It placed individual company growth inside a longer community story.
That cycle depends on willingness as well as wealth. A founder who has learned how to build can later become an advisor, an investor or the person making a timely introduction. Gilbert’s work creates occasions for that handoff. The benefit is personal before it is regional: somebody gets to ask a person with relevant experience what to do next.
Making another route for capital
Gilbert continues to argue publicly that growing companies need experienced operators alongside money. In a LinkedIn post welcoming venture advisor Matt Buchholz, she pointed to people who have built companies, executed complex deals and navigated growth. Her emphasis was on getting that insight to a founder at the moment it can help.
Her regulatory connections offer another view of the same problem. The Alberta Securities Commission lists her on its New Economy Advisory Committee, which considers innovation, access to capital and investor protection. That brings her work close to the rules under which private investment happens, as well as to the founders and investors trying to use them.
In May 2026, DealPoint and Dentons announced a venture fund platform for emerging managers. The offering combines legal documentation, formation, administration, onboarding and reporting. It extends Gilbert’s interest in making private capital practical, this time for people assembling a fund rather than closing a single company’s raise. Another promising conversation acquires a set of tasks that need to be finished.
Calgary Economic Development also listed her as an InterGen CEO panelist for its October 6, 2026 Economic Outlook event. Her working territory now spans individual founders, investment processes and the city’s wider business conversation. Through those different rooms runs the same question: how do the people already here become useful to the businesses being built here?
A second act sounds like a personal luxury until it becomes somebody else’s missing introduction. Gilbert’s work gives it an address in the everyday business of Calgary: a conversation, an experienced operator, a completed investment. The next chapter needs people. She has spent much of her career helping them find one another.