How to hire and build a rockstar sales team (ft. Justin Ouyang, former Director of Sales Strategy & Operations at Slack)

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by Mohammed Shehu

Justin Ouyang gets a nagging feeling after every movie or TV show.

As the credits roll, he heads over to Wikipedia and Google to look up everything about the episode, its actors and plot, and the production crew to make sure he didn’t miss anything.

This quirky ‘completionist’ trait, as he calls it, is perhaps fitting for a man who has prided himself on being thorough in every aspect of his sales and investing career — from account management to startup selection.

As the former Director of Sales Strategy & Operations at Slack and now an investor at OMERS Ventures, Justin shared with us his career trajectory, thoughts on sales strategy, and his advice for sales managers looking to build highly productive teams.

How to apply the hunter/farmer approach to sales

Coming in from an asset management role at Cambridge Associates, Justin shifted to running BizOps and sales at different companies like Zenefits, Intercom, and Slack. He quickly settled into a mindset of owning his output — a key trait required of any results-driven sales professional.

“At a firm like Cambridge Associates, I was the 1000th consulting associate at that level, and you’re kind of a cog in the machine. But when you join a startup, you really need to act like an owner and continue to deliver impact.” — JO

But once you’ve been in sales long enough, you quickly realize that not all sales approaches are created equal. Sometimes, sales teams need to know when to put down the hunting spear and pick up the farming scythe, or vice versa. This is part of the Hunter/Farmer sales dynamic.

The model is fairly simple: hunters (usually Account Executives) go into the wild to find new clients and close them while farmers (usually Account Managers) nurture and tend to their clients for long-term harvests and renewals. The right strategy for you will depend on your business model, budget, adoption rate, churn rate, and usage trends.

Hunters are heavy on outbound sales, while farmers prefer inbound inquiries driven through informative content and sales support documents. Justin’s career has afforded him both experiences: first with shifting Intercom to a hunter/farmer model and then with AEs owning both new business and expansion at Slack.

“Account executives have that skill set where they can break down barriers and move into other departments. With account managers or relationship managers, those skillsets are more about expanding usage and adoption.” — JO

How to raise funding as a B2B SaaS company

The Ontario Municipal Employees Retirement System (OMERS) is a $100 billion pension plan based in Ontario that serves over 500,000 and 1,000 employers.

The plan supports different municipal employees of Ontario such as firefighters and paramedics, and it is one of the only such funds with an early-stage investing arm, with offices in Toronto, London, and the Bay Area.

And while Justin mainly focuses on B2B SaaS investments, his colleagues handle investments in insurtech, health tech, and proptech. They also have a growth equity fund, a private equity team, and a direct capital markets & real estate team.

“I think B2B SaaS, the area I’m focused on, is probably the most competitive within the U.S. For a lot of our portfolio companies, we have many opportunities to connect them with different leaders and owners across the board.” — JO

OMERS Ventures’ sales tech stack

OMERS Ventures tech stack

* Crunchbase is a portfolio company of OMERS Ventures

A typical day-to-day sales role at a B2B SaaS company doesn’t allow for much dedicated learning, as you’re too busy running from meeting to meeting and putting out fires. Justin’s job, however, requires him to actively block off time to learn about the companies he’s investing in, the environments they’re playing in, and the problems they face.

His startup selection criteria boil down to three things: Team, TAM (Total Addressable Market), and Product. Team-wise, specifically, he looks for smart, humble, and detail-oriented founders who can clearly articulate their vision, business environment, and product — especially to a large audience.

“I think about whether they can attract and recruit top talent, especially in a market like this. Do people sign up for their vision and want to join them on building that journey? Can they paint a vision beyond the short term to like five to 10 years ahead, and do I agree with that worldview?” — JO

More importantly, founding teams need to be adaptable because the initial version of a product or company won’t remain the same throughout its lifecycle, as market and product pressures force it to evolve. Justin is especially proud of Postal.io, the San Luis Obispo-based offline marketing and gifting platform that has raised $34m as of writing.

“I was left fired up after meeting with the [Postal] founders and team. We spent a couple of days meeting with the go-to-market team, did some product deep dives, and went through the FY23 plan at the board meeting. I think Eric and Jed have built a strong culture where people are excited to work together, work hard, and win.” — JO

Hiring for roles in Sales Ops and BizOps? Keep these tips in mind

For BizOps and SalesOps roles, it’s never just about the job description. By definition, people in those roles are responsible for everything that the Business or Sales teams don’t do, respectively.

Being adaptable to those responsibilities — and having a hands-on approach to getting the job done — can greatly boost one’s success in those fields and drive results for their team. It’s these qualities that Justin looks for in candidates he hires.

“I think that combination of traits — “smart and humble” — is incredibly important, because those are the people you want to be in the trenches with. And I expect people to show up prepared and ready to go. So be on time and do your homework on the company and on the role, and show why you’re a good fit.” — JO

But the advice goes both ways. For employers, attracting, recruiting, and retaining talent has only become more important over the past few months thanks to rapidly shifting trends in employee turnover.

To retain top-class talent, it’s important for sales leaders to have regular 1-on-1s to discuss career growth opportunities with their team members. They should ideally include a skip-level meeting (meeting with your boss’s boss) to help sales pros build the right connections with their company’s leadership.

“It helps an individual feel like everybody’s invested in their career. Those two people are the most important in deciding whether that person likes their job and what their career track looks like at that given company, so I’m a big advocate for that.” — JO

Like many other leaders we’ve spoken to, Justin emphasizes the importance of constant learning, building the right relationships, learning how to manage up, and getting mentors involved in one’s career growth and job performance.

“I’m just addicted to learning. If you’re putting yourself in BizOps roles or joining venture capital, you are drawn to the broken glass. You like problem-solving, you like learning, and you try to find yourself in roles that maximize that, and that’s what I’ve seen throughout my career.” — JO

Struggling to stay productive? Use your calendar

It’s a nifty little tool we all carry around in our pockets, but few of us use our calendar to its full potential. Justin is a huge proponent of structuring his day using his calendar — a hack he suggests for anyone struggling to stay productive.

“I use my calendar religiously. If it’s not on my calendar, I’m not doing it. I go exactly where my calendar tells me — so obviously I have different Zoom meetings and events that I attend — but I also block off time for learning, reading, to-do lists, etc.” — JO

Looking to boost your career? Travel to more countries

Justin’s one regret was that he never got to live and work in more countries when he was younger. It’s not an unfounded regret, either - research shows that international work experience has a positive impact on your career, whether you’re a lawyer, engineer, or banker.

“There’s something about living and working in a different country and culture. It really expands your perspectives and worldview, and it just seems really cool to me.” — JO

And if Justin wasn’t working in tech, David Attenborough would’ve received a call from him about an internship. To Justin, the opportunity to live and work all over the world, documenting nature’s amazing places, sounds like a dream.

“His documentaries are just him going to amazing places all over the world. He’s usually lying on an iceberg next to a seal documenting something and narrating at the same time. I would love to be that guy’s intern and just travel with him and learn from him.” — JO

We can get on board with that, Justin.

You can connect with Justin Ouyang on LinkedIn or Twitter.

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