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From negotiating to fundraising to strategy, tech leaders shared their top insights in front of a crowd of 600 of the tech community's finest.

A packed house at RBC WaterPark Place was treated to five presentations by tech leaders and start-up founders who shared concise, tangible lessons from their journeys in tech so far.

1. The Secret to Effective Negotiating

Adrian Joaquin, Founder and CEO of Workhaus used to be a chiropractor. Like many founders before him, he started his company out of personal necessity: He needed to find a place to work while he was looking to start a new company.

Joaquin is often asked, “What the heck did you take from being a chiropractor to the business world?” His answer: How to be an effective negotiator.

While the two worlds are seemingly far apart, Joaquin shared that some skills — like negotiation — are transferrable.

“In negotiations, it’s not winner take all,” he said. “You’ve got to listen very intently to the needs of the other side, and you need to get a full picture of what’s going on,” he said.

Understanding what the other side’s motivations are helps you communicate what you need and what you want. His experience listening to the needs of his patients has helped him go to landlords and negotiate big deals. “Deals that we didn’t have business doing at that point,” he admitted.

2. Five Lessons Learned About Strategy

Nina Bilimoria Angelo, VP of Product Marketing at Top Hat shared 5 lessons learned about strategy in her presentation entitled “The Art of Choice.”

Strategy is choice.

“Strategy about making integrated choices about where to play and how to win,” Angelo began. Your playing field includes your segment, product categories, audience, etc. And how to win is defined as your competitive advantage, or your distinctive position.

Angelo called out Roger Martin — former Dean of the Rotman School of Business and currently ranked as the top management thinker in the world — as an example of making integrated, distinctive choices. Known for his work in Integrative Thinking, Martin became chair of Tennis Canada in 2005. While there, he and his team led the forging of a strategy for playing to win globally in tennis.

He knew they needed to make bold, distinctive choices if they were going to play to win. They appointed Bob Brett, one of the world’s legendary coaches, as head of their Under-14 program. They changed their athlete funding strategy and enforced adherence to the strategy through the successive three-year chairmanships. The result? In the last six years, Canada has seen three players become Grand Slam Finalists, and one become the first Canadian ever to win the U.S. Open.

It’s important to decide what you’re NOT going to do and where you’re not going to play.

Agreeing on your market fit and where you’re not going to win is essential to thriving in technology.

Write down your strategy.

This step helps your team get aligned and make the tough decisions. Writing down your strategy also allows you to share it, and communicate to your team how strategy impacts day-to-day activity.

Regularly hone your strategy.

Your strategy needs to keep up with market trends and competitors. At Top Hat, they revisit their strategy on a campaign basis — which is every four months. Regular check-ins are important for a startup who wants to thrive in a dynamic market.

Strategy without tactics is the slowest path to victory.

Tactics matter, as does measuring success.

3. Lessons Learned on a Fundraising Tour

The Raise of the Month featured Ada Support, where CEO and Co-Founder Mike Murchison shared fundraising lessons learned from a few rounds of fundraising.

Fundraising is a hiring process. “There is a power dynamic that exists in any VC meeting and it’s your job to break that balance,” Murchison started by saying. He advised attendees to interview the VC you’re meeting and ask them the same questions you’d ask a future colleague or member of the board. “This approach can help you find truly great VC’s who can move the needle for you. A great VC add s far more than capital,” he said.

Be an outlier. “It’s shocking to me how many people follow the motions of fundraising,” said Murchison, saying that most companies go into a VC meeting with the same kind of ten page deck. “Venture is fundamentally a business in search of an outlier — you want to break the script and stand out,” he said. It’s important to make things a bit uncomfortable and challenge the status quo. This is what gives you a shot to really capture attention.

Engineer Momentum. Fundraising can be such a distraction to a business, and many founders worry about losing momentum when raising capital. That’s why it is, “Super important to raise at right time, and that as you raise you’re continuing to tell a story of momentum in your business,” advised Murchison. One way to do this is to not say everything that’s great about your company in the first meeting — it’s really valuable to follow up with another tidbit in the next one.

4. Lessons Learned from Scaling an Engineering Team

Marc Staveley, CTO of Index Exchange, shared insights about scaling an engineering team. Index Exchange, an Ad Tech company which runs auctions with creative suppliers, has 200 engineers right now — 86 of whom they added this year.

In growing so fast, how do you make a team mesh? Here’s how Staveley did it:

A self-directed agile environment. Smaller, self-organized, self-directed teams are needed when growing that quickly. “You can’t do a command and control style,” Staveley said. “Your teams need to understand what the vision is, so they know what products they’re building and why they’re building them.”

A shift from systems-based engineering to a business-value focus. When teams understand the value of the products they’re building, it’s easier for them to buy into the vision.

An opportunity to fail safely. Index Exchange has processes in place where when code gets to production, it’s OK to fail. This produces an environment where if the team creates bad code, it’s OK. They can simply try again, no harm done.

Staveley shared five tactics to successfully scale an engineering company:
  • Bring in diversity of thought
  • Train your teams and invest in being agile
  • Institute in-house agile delivery coaches
  • Create and develop a DevOps Culture
  • Give your engineers interesting problems to work on

5. How to Turn a Legacy Brand into a Hub of Innovation

Michael Lysaght, Chief Digital Officer of WW (formerly Weight Watchers), was last to speak. When looking for a new challenge, he was asked to consider joining the technology team at WW. In doing some initial research, he found first that the website was down. When he did get in, he found a flash-based food tracker that hadn’t been updated in over a decade.

He became obsessed with the idea of disrupting from within a brand, knowing he could take the principles learned from the start-up world and apply them to an established brand.

Here’s how he did it:
  • By embracing modern technologies. He felt that technologies such as Swift, Kotlin, React, Scala, Node, Cloud and Kubernetes were going to allow them to move faster.
  • By looking at their practices. They embraced Agile and knew that a user-centered and lean design would solve their members’ needs. Wanting to enable engineers to push code whenever they wanted to, they moved from two releases per year to several thousand deployments last year.
  • By focusing on their people. They reorganized their team structures and hired 700 world class people across several functions.
  • By underpinning it all with culture. “This is the really important secret sauce,” Lysaght said. “We needed to create an environment that empowered teams to innovate.”

As such they have created a platform that allows teams to innovate at a really inspiring place. When Lysaght started, their app was at a one-star rating — now, with over 725,000 ratings, they’re at 4.8 stars. Lysaght is quick to point out that everyone’s work is reflected in these ratings.

“By focusing on technology, process, people, culture and brand we have turned a legacy brand into a hub of innovation. It’s possible for everybody to truly innovate — it’s not just for start-ups.”

Don’t miss more inspiring and insightful lessons from tech leaders. Head to the next TechTO on October 21, 2019 from 6-9 pm!

Don't miss more inspiring and insightful lessons from tech leaders. Head to the next TechTO on October 21, 2019 from 6-9 pm!

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