Skip to content

Lessons Learned from a VP of Sales

Jim Farrell recently joined one of the Wesley Clover portfolio companies, Solink, as Vice President of Sales. With nearly twenty years of experience working in sales within the tech sector in both the Canadian and American tech ecosystems, Jim has gained the perspective needed to understand what works, what doesn’t, and how to deal with the common obstacles and challenges that leaders in this industry face. He’s used this knowledge to help the companies he has worked for successfully grow.

Twenty years in tech, at a glance

Starting in 1996 as a Canadian federal government employee, Jim began working with document search and archiving as litigation evolved from strictly paper documents to also include digital documents, emails in particular.

Since then, Jim has been a part of five different acquisitions, and has gained experience in selling traditional software, software as a service (SaaS), and infrastructure as a service (IaaS). He has sold both channel sales and direct sales while working for Ottawa based companies and Bay Area based companies. Jim’s experience has ranged from selling to “two Devs and a Dog” (SMB) all the way up to some of the largest companies and government agencies in the world (enterprise).

By going through the different acquisitions, including Samsung’s purchase of Joyent and HP’s eventual acquisition of Autonomy Inc., Jim’s been able to see first-hand how small teams with big ideas grow, succeed, and sometimes fail. As he’s watched the ups and downs of founders and friends navigate the process of expanding, finding funding, getting acquired, and (sometimes) starting over, he’s learned a lot of lessons that he has graciously shared with us.

What it takes to sell SaaS successfully

Jim’s career has helped him gain a comprehensive understanding of how to grow small companies that sell tech solutions. He’s been in the middle of the industry as the changes that cloud technology has brought have unfolded. Over the years, he’s become increasingly interested in joining smaller teams that allow him to leverage his experience, building out strategies that contribute to rapid, yet sustainable growth.

He says there are a few key lessons to take away from his experience as both a leading salesperson and an employee of SaaS, IaaS, and cloud-focused tech companies.

Lesson #1: Stay curious, keep learning

Whether you’re learning about a new feature of your product, an innovative technology to use, or simply getting to know your customer and mapping out their journey, succeeding in your endeavours requires staying curious and being open to learning, regardless of the role you play within a company.

As a salesperson, it’s critical to understand why your customers need, want, or love your product. In order to understand that, you must map out your customer journey and that can only be done by talking to them and being genuinely interested in the value that the customer is searching for (and hopefully finding) in your offering. If you know why (and, in particular, when) the customer falls in love with the product and at what point they begin to see the value of that product, you’re much more able to relate to them and they are much more willing to listen to you.

Jim’s seen the tendency of customers to lump SaaS salespeople in with the salespeople of the old guard – door-to-door salesmen, car dealership salespeople, telemarketers, and all the other salespeople we all try to avoid with a ten-foot pole. But he says SaaS isn’t like that because, most of the time, it is actually created to help someone solve a problem or complete a task better, faster, and/or more effectively.

Understanding where those moments of ease and relief happen within the customer journey and how they impact the customer’s workflow are critical to being able to sell the product well. And that understanding can only come from curiosity and a lifelong dedication and willingness to learn something new.

Lesson #2: Ask great questions to see the bigger picture

Going hand in hand with staying curious and constantly learning, another great piece of advice that Jim lives by and encourages his teams to pick up as well, is asking questions. No matter what role you have within a company or how long you’ve been there, it’s important to keep fueling your curiosity and love for learning. But don’t ask just (m)any questions. Instead, ask great, well-framed, thought-provoking questions.

Jim’s learned that there are two main approaches to asking questions and how you ask them will alter the type of answer you receive. The first is through the eyes of an investigator, a nod to his years of working with litigation and discovery management companies. The second is through the eyes of a curious and interested colleague. Jim says that there is a certain finesse and balance required in asking questions to instill a sense of trust and honesty in the other party and, in his experience, he’s learned the most useful information from coworkers and customers when having a genuine, open, and honest conversation about processes and products. Finding out what’s great already, as well as what could use improvement, is key in being able to develop a successful offering.

The trick to asking great questions is thinking about how you can help that person and how that person can help you. Are you talking to a customer? How can you (or your product) solve the problem they need a solution to? Are you talking to a colleague? How can your role within the company help make their job easier? On the flipside, how can the knowledge that the customer and/or the colleague has help you do your job better? Always be open to a conversation and breed an environment of trust in order to ensure that everyone you come into contact with has a safe space to be honest and share the kernels of knowledge they have through their own unique perspective.

Advice for a leadership team

Jim encourages founders and executives within a company to foster a communicative atmosphere that doesn’t just seclude people or teams in separate silos that never interact with one another.

One of his favourite things about working in tech and with SaaS companies is the opportunity to talk to people in various roles in order to get a better understanding of all of the facets at play. A developer will have a very different opinion about what the best or coolest feature of a product is than a customer success representative. A CEO will promote their company in a different way than a salesperson would. A data analyst will get excited about a different aspect of the software than a product manager.

Each person’s perspective is defined by their experience and their role within the company and, without being able to understand how all of those moving parts fit within the bigger picture, the leadership of that company might simply overlook some of the most exciting and useful things about the product.

One of Jim’s favourite questions to ask anyone and everyone within a company is: “If you could wave a magic wand and change one thing about this company to make it great, what would that one thing be?” The answers he’s gotten have sometimes taken a while to formulate, but have always led to learning something new and using that knowledge to create something better.

Another piece of advice Jim offers to founders is to not be afraid to bring in the right level of experience conducive to rapid, sustainable growth. Especially when still in those early stages, it can be a real challenge to do everything required for success without the knowledge needed to achieve it. And that knowledge can only come from leveraging people with the right amount of experience.

“If you aren’t hiring people that are ten times better than you, your company won’t last.” – Mike Matta, CEO of Solink

Lesson #3: The payday should never be your motivation

Many people see the tech industry as some sort of holy grail for wealth and success. The amount of money that the industry creates is an easy attraction for the young entrepreneurs of today that believe that their idea is the next billion dollar unicorn.

But Jim says that if you enter this sector simply waiting for that big payday to come, you’re missing the point, and you’re also largely missing the opportunity that exists to create something that has intrinsic value to customers and employees alike. It’s the adventure and the risk that should motivate you to enter startup life and that’s why it’s not really for the faint of heart or for those just looking to make a quick profit. Your main drive should be a healthy appetite to keep working with your team to develop a useful product. Don’t worry about the investments that are happening around you and don’t solely focus on the growth or sale or business aspect. Instead, focus on creating something useful with people you believe in. Hire people that find joy in the uncertainty and the endless possibilities and make and maintain relationships with the people that believe in you too.

That love of adventure and learning is what Jim looks for in the companies he works with, as well as the people he hires to join those companies in the sales department. Talented young salespeople often have no proven track record, but they do have a love of learning and a natural penchant for curiosity. They want to get to know more about the product, about the customers, and about the team behind it all. And the most successful ones have their own approach to extrapolating the value in that company or product and explaining it to others.

There is no magic formula; no amount of reading and regurgitating sales books will make someone good at selling if they have no desire to learn, unlearn, and relearn as the company, team, product, and industry continues to evolve.

Lesson #4: The product should sell itself

A lot of early-stage SaaS companies make a couple of mistakes at the beginning of their development which can set them back right when they need to be getting ahead. Although this may sound counter-intuitive coming from a salesperson, Jim’s found that these companies tend to pump a lot of money into a sales and/or marketing team before really creating a valuable product and understanding that product’s customer journey.

Instead of spending that time and those resources on getting the audience and then building out the product, Jim says early-stage startups should focus on getting the product to a point where it sells itself. “A product that people want to buy should be able to confirm its value, establish new value, establish stickiness with customers, and provide the updates and training needed on its own.” A good sales team and marketing department is supporting an already amazing product, not propping it up.

A key aspect of successfully selling and boosting growth rapidly is having an amazing product that the team behind it believes in. Your product should be developed in such a way that it provides customers with “a remarkable experience that they want to tell their friends about”. Don’t bloat your offering with things it doesn’t need. Instead, think of the apps you like, the services you use regularly, and the reasons behind why you like and use them. Then apply those same principles to your own idea.

Create a product that people actually like using and build your company around that product. The sales and marketing efforts should be complementary to an already amazing innovation, highlighting the various features that appeal to each perspective and persona in your customer base. If your team doesn’t believe in the product, no amount of fancy design or persuasive sales lingo will fix that and all you’ll be doing is contributing to an increased amount of customer churn later on.

Lesson #5: Foster opportunities to share knowledge in your community

The biggest thing that Jim sees as missing in the Canadian tech ecosystem at the moment is that established sense of community and friendly competition that is an inherent part of the Silicon Valley ecosystem.

In the Valley, you can have a two hour long conversation with someone you meet at the bar that will change how you look at your next six months as a growing company.

Companies and networks of people are much more willing to help one another through informal and formal relationships and there is an attitude of abundance and sharing the wealth that hasn’t yet reached Canada’s somewhat isolated tech hubs. It seems like the attitude in Canada is still more about securing proprietary rights and protecting great ideas (perhaps too much initially).

Fostering that same level of comfort, openness, and interaction is an important step in boosting Canadian tech communities. That’s why Jim has been thrilled to join Solink, and the larger Wesley Clover and Alacrity Foundation family by association. He’s seen that type of thought-provoking engagement and collaboration within the Wesley Clover portfolio companies and he’s been excited to get to know more about what they each do and how they can help one another.

Initiatives and conferences like SaaS North are breeding an atmosphere of camaraderie and community as well, helping more small companies with big ideas connect and find out how they can work together to bolster the overall success of the industry.

Startup life is hard, but worth it

These days, Jim prefers working with early-stage SaaS companies because he can use his years of experience to guide and direct energetic teams through those awkward teenage years of growth. Although “startup life is hard”, he says it’s also incredibly rewarding and exciting because of its quick pace and constant evolution.

Adding his experience to Solink, a company that focuses on cloud-based solutions for video recording, loss prevention, and investigations, seems like a perfect marriage of Jim’s previous experience with discovery and investigatory processes and his love of SaaS, cloud, and innovative technology. The Solink team is also very excited to have him join their ranks.

“Jim is an awesome addition to the team – his combination of sales and product chops makes him an invaluable resource as we move from product-market-fit to ‘rinse & repeat’ factory. We are EXCITED to have him on-board.” – Mike Matta, CEO of Solink

With a long-term goal of being an entrepreneur and a lifetime of knowledge gained through his journey, Jim’s aim is to use all of the experiences he’s had over the years to one day run his own company. But, until then, he’s happy contributing to the growth of other companies, particularly those that are still establishing themselves as industry leaders.

Return to top