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Q&A: Paul Teshima, CEO & Co-founder,, on how to build a sales team that scales

One of the most important — and hardest — aspects of running a scaleup is figuring out how to transition sales from being founder- to team-driven.



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#ScaleStrategy is produced by DX Journal and OneEleven. This editorial series delivers insights, advice, and practical recommendations to innovative and disruptive entrepreneurs and intrapreneurs.

One of the most important — and hardest — aspects of running a scaleup is figuring out how to transition sales from being founder- to team-driven. Paul Teshima, CEO and co-founder of, knows how important it is to growth.

Teshima is a Canadian-born serial entrepreneur who, as part of Eloqua’s executive team, grew that company to more than $100 million in revenue over 13 years before it was acquired by Oracle for US$957 million in 2012.

In 2014, Teshima launched, a relationship intelligence platform that helps businesses find and build the right relationships to drive revenue. He secured an office in OneEleven and along with his co-founder Steve Woods (also a co-founder at Eloqua), and they have grown the company to 22 employees, landed several major enterprise clients and more than 20,000 B2B users on the platform.

Teshima spoke with Bilal Khan, Managing Partner of M6ix Ventures and the founding CEO of OneEleven, about the hard parts of scaling a sales team. (Read our full story on here)

Bilal Khan: How did you manage the transition of startup to scaleup when founders go from being the primary salespeople to building out the sales team?

Paul Teshima: One of the most important aspects of scaleups is figuring out how to transition sales from being a sales team of one as a founder to a sales team. It’s also one of the hardest. Founders often overestimate how much they actually know that no one else knows, decisions that they can make in their brains at the drop of a hat in a deal cycle. It’s really important to try and simplify and understand what could be translated salesperson that they can then repeat over and over again.

I also think that first hire is super critical to be much more of an entrepreneurial sales person. A classic best practice as you continue to scale is hiring them in groups of two so that you can start removing variables because it may not be the right time to transition it you didn’t hire someone with the right skills. That stage is really delicate and you will need to be patient.

Khan: Have you transitioned into a sales team approach as opposed to the founders?

Teshima: I’d say that we’re still in founders plus a bit of hybrid sales teams. So we’ve got some salespeople working on that delicate transition period now. I can tell you that I’m already overestimating how much I think they know because I know and take it for granted. I mean, of course they don’t know, it’s in my brain still. It’s about being methodical. We just brought someone in to help us really try and simplify the sales process to determine what can be scalable.  

Khan: When do you start thinking about finding a seasoned sales leader? Do you immediately find someone who can start building a sales machine or is this further down the road once you hit your stride?

Teshima: It depends on where you are on a revenue curve plus the capital you have and the talent that’s available at the time. There’s definitely an argument that you hire the Director of Sales first that can carry the bag and helps to scale that initial phase. But there’s also an argument about hiring a hands-off VP to go build up the entire team. Both require early evidence of some form of scaling. You have some sort of process that defines how the sales process works today and there’s some of the things that we know in terms of the metrics about it.

Khan: What are some of the key metrics for a sales success that you think are important?

Teshima: There’s obviously the output of generating revenue in the growth program. For us, we’re in a product-led model so it’s a little bit different and a little newer. We look at early stage interest as signing up for a user, finding a cluster of users account — is it qualified product lead? — and then we ask if we can turn that into a trial that converts to a paying customer. We look at those stages which is a little different than the classic B2B funnel.

Khan: In Canada, we talk a lot about whether we have the sales professionals with the deep skill set to be able to scale companies and do B2B sales. Has finding sales talent been a struggle for you?

Teshima: Are there less seasoned salespeople in Canada who have gone from $0 to $100M than in the Valley? Yes. Do we need to solve that problem? Absolutely.

I’ve been lucky that I’ve been part of the business that has gone from $0 to $100M in revenue (Eloqua) and we didn’t have anyone to rely on but ourselves. I think it’s just a matter of going in and doing it. You are seeing lot of seasoned people coming back to Toronto and as that continues to happen you’re going to see those people train others to get to the next scaling point.

[Sales] is really about the discipline of keeping in contact and helping others in your network, knowing that it will pay back over the long term. We did a study where we showed that the average head of sales has a strong network at work that’s three times the size of an sales development rep, which makes sense.

Khan: I wanted to talk about B2B sales cycles. Those are really challenging time frames in cycles to manage when you’re starting a company. How have you hacked in on the early stages of the sales cycle from a simple cash-flow perspective?

Teshima: The hardest part of closing an enterprise deal is first finding it and then getting involved in the sales cycle itself because they’re so inundated with a barrage of outbound outreach from all these customers. The strategy I recommend to scaleups is this: You have to show some pocketed value, lock them in and then go division-to-division quickly. And do it cheaper than a competitor. Try that approach versus just the top down approach right out of the gate.

Khan: Would you do that at the expense of generating any revenue?

Teshima: Enterprises today actually have slush funds to experiment with technology where they didn’t before. It is absolutely true that if they put some skin in the game, you’ll have a more successful pilot. This opportunity allows you to qualify those deals earlier. I think you need to be pretty disciplined about qualifying and if you invest in the cycles and then put a price on it.

Khan: So you’ve landed the customer and they are paying for the product offering. You’re coming to a renewal cycle and they scale back their offer. How do you address a situation like that?

Teshima: We haven’t had that happen at If I think back to me earlier days at Eloqua, there were times when customers pulled back. It’s only a death cycle if you don’t learn from it for the other customers that are existing. You should never forget that customers can always come back in and in champions can always move jobs. You always want to do right in those situations because you never know when you’re gonna meet them next in the ecosystem. Maybe they’ll evaluate it differently.

Khan: How do you think through channel partners strategically?

Teshima: In cloud software, it’s more challenging to have channel partners because of the nature of the product. On the technology side, there is probably good synergies. On the service consulting side, I think it’s harder. If you think training your first salesperson is hard, try training channel partners all your stuff, when they have 20 competing things to sell and they’re making a small margin on your product.

You first need to establish that you can direct sell your product in a repeated way before you think about channel partners. You can get lucky and find one strategic one and go big, but more often than not you’re going to find that they’ll get all excited, get trained and they’re not going to sell anything. Even if they do close something, maybe it’s not exactly the right fit. I’d say be careful with channel partners in early stages.

Khan:  Are there any books that helped you in your scale journey?

Teshima: I am probably less of a book guy than I should be as a CEO. There are two books, however, that I found helpful:

  • Jim Collins’ book “Good to Great”. I especially liked chapter five about managers and this idea that the best managers, CEOs and executives don’t even want the spotlight. They’re much better being extremely streamlined and determinedly humble, inwardly focused on driving change.
  • “Switch” by Chip and Dan Heath. One thing that came out of that was this idea of focusing on the bright spot in your startup. As a founder, you’re geared towards focusing on what needs fixing. It’s actually better and more uplifting for the business to focus on the bright spots.

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Women are great cybersecurity hires. So why are they so underrepresented in a short-staffed field?

How can the sector counter factors like sexism, internalized bias, and barriers to entry.



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In January 2023, the Canadian Centre for Cyber Security (CCCS) delivered its baseline cyber threat assessment with a stark warning: organized cybercrime, it said, “will very likely pose a threat to Canada’s national security and economic prosperity over the next two years.”

Possible targets cited by CCCS included hospitals, where cyberattacks can disrupt patient care and delay tests; goods and services, where they can drive up prices and short supply; and of course, banking attacks, payment card frauds, and identity theft. 

Cybersecurity, consequently, is a fast-growing field where the stakes are already relentlessly high and only promise to grow — but not only because the threats are multiplying.

The number of vacant cybersecurity positions globally outpace the skilled workers available to fill them, and according to IT World Canada, this means the escalating likelihood of cyberattacks are expected to be exacerbated even further by the sector’s chronic talent shortage. 

Canada is not exempt from this problem. The Information and Communications Technology Council (ICTC), a digital research-based not-for-profit, reported in a 2021 study that despite offering robust, competitive salaries, one in six Canadian cybersecurity positions go unfilled.

That represents about 25,000 jobs left open — attributed partly to burnout, students opting out of cybersecurity programs while they’re still in school, and competition from U.S. companies offering higher salaries, the study read.

But while the nation faces a shortage of workers, ICTC’s research also suggested a lack of diversity in the talent pool could prolong it: those identifying as Black, Indigenous, or people of colour represented only 25% of cybersecurity workers. 

Those identifying as women had the least representation — just 20%.

“We need to pull more women in,” Rushmi Hasham told DX Journal in September.

Hasham is the director of cybersecurity workforce training at Toronto Metropolitan University’s Rogers Cybersecure Catalyst, which offers innovative training and certification programs aimed at boosting Canada’s competitiveness in the sector.

And although Hasham says more women are beginning to pursue cybersecurity, increased representation is necessary to perpetuate that progress — and the valuable contributions women make to the field.

“We want to have their opinions heard, we want their unique perspective, and women offer new solutions that we need, frankly, across the entire industry,” she said.

“But we also need to make sure that we’re creating the space, that they feel the inclusion.” 

The value women bring to cybersecurity

Cultivating a gender-diverse staff offers a litany of benefits for companies, and when it comes to cybersecurity, there are practical, research-based incentives to hire women. 

Université du Québec à Montréal professors Camélia Radu and Nadia Smaili found “evidence of a positive association between the level of cybersecurity disclosure and board gender diversity” in their 2021 research study, Board Gender Diversity and Corporate Response to Cyber Risk: Evidence from Cybersecurity Related Disclosure.

“The presence of women IT experts on boards resulted in improved cyber risk management — board monitoring, management supervision and corporate governance in particular,” Radu and Smaili wrote for The Conversation in December of 2022.

In addition to bringing new perspectives to the decision-making process and adding a greater variety of skills and capabilities, they said their research also found that women “had lower risk tolerance, enhanced ethical practices and engaged less in fraudulent practices.”

In short?

“These specific skills, combined with their IT expertise, meant women improved the cybersecurity risk monitoring of their companies,” Radu and Smaili said.

But despite all they bring to the table, The Globe and Mail’s Tayo Bero wrote in August 2022 that women continue to face barriers in the industry that include being talked over in meetings, having their ideas ignored or co-opted by their male colleagues, and never being recognized for their work.

The effects on women’s cybersecurity careers are detrimental. 

“Obviously, if a [young woman] sees this type of treatment towards her where she is constantly reminded that she has to prove herself [and prove] that she actually knows something, she would think twice whether this is a good career for her,” Natalia Stakhanova, an associate professor of computer science at the University of Saskatchewan and a Canada Research Chair in security and privacy, told Bero.

Research also suggests women are also less likely to apply for cybersecurity jobs in the first place.

According to a survey commissioned by Microsoft Security, men are more likely than women to feel qualified to apply for a cybersecurity job posting, while many respondents “indicated a bias that cybersecurity isn’t a traditional career choice for women.”

“Some women expressed these biases themselves,” Vasu Jakkal, the corporate vice president of security, compliance, identity, and management with Microsoft, wrote in a March 2022 blog post.

“The survey indicated women are more likely than men … to think that cybersecurity is ‘too complex’ of a career.”

This perception could be influenced by the shortage of women in the industry — possibly creating a self-fulfilling, and perpetuating, prophecy. 

“A lack of representation can then reinforce the gender gap by dissuading women from entering cybersecurity,” Jakkal said.

How to improve equity and inclusion in cybersecurity

With challenges like these at play, Hasham believes that we can start attracting women to cybersecurity jobs by lowering barriers to entry.

“If we’re looking at the mid-career woman making a pivot, she’s looking at: can I put my family aside? How do I do this?” Hasham said. “So, time is a barrier.”

Hasham’s work has been closely tied to the development of solutions that include rapid workforce programs like Toronto Metropolitan University’s Accelerated Cybersecurity Training Program, which took students six months rather than years to complete.

It has since been replaced by Certifications for Leadership in Cybersecurity (CLIC), but the goal, she explains, remains the same: to boost the number of qualified individuals entering the cybersecurity workforce while increasing representation.

Delivered online and taken part-time, CLIC is both self-directed and instructor-led, has a focus on mentorship, and is designed to be thorough: within six months, graduates join the labour pool having attained two globally-recognized SANS GIAC certifications.

“Women always think, ‘If I’m going into training, what will the return be?’ And then: ‘That investment is coming out of my family budget. Can I really do this?’” Hasham said.

“It’s about putting ourselves first. We really don’t.” 

Hasham also suggests that women who don’t apply for cybersecurity roles because they don’t exactly meet the qualifications in the job description should reconsider. 

“A woman will say, ‘Oh, they wanted these certifications, but my certifications are [different],’” she said. “And then, she doesn’t apply. But meanwhile, all of the skill requirements are what she has, and more.”

Once women secure jobs in cybersecurity, they need allies in the workplace, Hasham said. And here, men and management have an important role to play in lifting their female counterparts up.

“We need men to be collaborating with us in that learning process, for them to be part of the solution,” Hasham said.

“We’ve gone through this notion that if we created women-only cohorts, women would succeed more. And we learned that men need to be part of that, because you’re going to work in a collaborative co-ed environment anyway. So, we need to create that in our training.” 

Finally, Hasham said that women in the industry need to be seen and heard so that others can imagine themselves in a similar role.

“It’s the full belief of: ‘If I see a woman in this profession, I can be a woman in this profession,” she said.

“We need to amplify the women who are in the industry. We need to give them a voice, we need to give them a platform. We need to help them shine.”

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Multiple generations help a workplace, but age isn’t everything

As it turns out, similarities across generations abound, with differences having more to do with life stages than arbitrary age groupings.



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Not long ago, workplaces had a certain structure. 

There was hierarchy and work hours. Some bucked the trends, but it wasn’t until the age of digital transformation interrupted our notions of work, life, and play that things got interesting. 

From the 1980s, when computer use was first introduced and left many older workers behind, to the rise of the internet and the modern workplace, where one survey found 77% of workers used a computer daily. That pace of change only increased with the pandemic and work-from-home arrangements facilitated by Zoom, Slack, and even surveillance. Automation and AI is set to further reshape the way we work.

Now, people are living longer, the cost of living is delaying retirements, and going to the office is not always a requirement. Startups follow the hours set by necessity and even sectors outside of tech are getting more flexible. 

That sort of change, and having those multiple generations bumping elbows, can have big rewards — but also poses challenges. 

Intergenerational learning and expectations around work hours, technology, and how to build a business can either clash or contribute to a more resilient workplace. Experience, mentorship, and a diversity of thought can help increase productivity and build a more stable workforce

But it can also lead to challenges, where comfort with technology varies and so do expectations around what a workplace can and should be. Those differences need to be recognized and managed in order to build a successful contemporary workplace.

Limiting the view to generations, however, is only a starting point. Similarities across generations abound, and differences have more to do with an individual’s stage of life rather than an arbitrary generational grouping. 

What the generations want 

A recent report and survey from staffing agency Robert Half looked at what motivates each generation, and found 95% of respondents see value in a multigenerational workforce — dispelling notions of antagonism between ‘lazy kids’ and ‘old timers’ getting in the way. 

Specifically, respondents liked having a wider range of perspectives and ideas, learning from those with different levels of experiences, and mentoring, among others. 

And it noted differences in what, broadly, generations want from work: 

  • Gen Z: looking for a “robust work experience” 
  • Millennials: want to contribute more in senior roles — and with more autonomy 
  • Gen X: eyeballing better compensation 
  • Boomers: the least concerned about AI impacting their work, and the least likely to retrain if it does

Workplaces need to be flexible and offer work-life balance, the report notes. And there will have to be some give or take to adapt to generational preferences, in order to attract and retain workers. 

But the report also shows that there is plenty of agreement among the groupings. The three youngest generations in the workforce all list a competitive salary and regular merit increases as their top influences on job satisfaction, and all three place fair workload and job expectations as the second influence. 

The benefits of experience

Sandi Gilbert, CEO of the aptly named InterGen, understands the power of an intergenerational workforce. Her company acts as a matchmaking service between experienced executives and nascent companies with big ideas who have identified gaps on their team.

“Young entrepreneurs, particularly tech entrepreneurs, certainly understand the problem they’re solving and how to solve that problem,” she says. “But they really don’t know how to build a business.”

The aforementioned executives might be bored after retirement, or missing the coffee meetings, conversations, and challenges that come from building something new. They help introduce a company to their networks and get access to a new network springing up around tech.

“It’s not just about gray hair, but it’s about diversity of thought, diversity of experience that actually creates a better well-rounded company,” says Gilbert.

That diversity of thought also introduces the more experienced workers to a world outside of the country clubs where they might congregate, or the board rooms dominated by men who look just like them. 

Some of those executives choose to stick around, while many help get a business established and then move on to the next challenge (or round of golf). 

That’s not to say there aren’t challenges. Adapting to a workplace that might not keep regular hours and offers flexibility between sessions of hard work can be uncomfortable for those accustomed to a more conservative work environment. 

“Sometimes those people that have had the luxury of working for a month on whether the company is going to move ahead with something, and you’re gonna make that decision in three days, that’s hard for them,” says Gilbert.

Young entrepreneurs also have to come in with an open mind, she says. Those who think they already have all the answers likely won’t listen to the knowledge and advice of the more senior executives. That can also increase the likelihood of conflict  

There can also be challenges across generations when it comes to technology tools and communication. 

Colleen Pound, CEO of Proxure, an AI professional services procurement platform, says things like introducing Slack or trying to give a laptop to an older colleague can highlight some of the generational differences in how to get things done. 

That can hold people back. 

“Especially in the age of energy transition and digital transformation, people are looking to start over or learn something new and that can be scary,” says Pound. 

“Young people are frustrated that older people don’t know how to work technology properly, and old people are scared to learn new tools because they’re unfamiliar, and they’re slow and they’re not as efficient, and they don’t want to make a mistake and have all their work be lost.”

But on her team, she says it’s less about the age and more about the attitude and aptitude of the person behind a particular workplace quirk. 

It’s not just age

Generations are a pretty easy way to group people, but like any catch-all designation they can fall well short of accuracy. 

Nathan Wawruck is Director of Permanent Placements at Robert Half, who produced the above report on generational differences and synergies. 

“I think age is a very convenient way to group people, but we have to look at all sorts of other factors, like how financially secure are they? How far away do they live from the office?” he says. “I think it’s interesting to get more granular beyond just the age.”

Wawruck’s job is to match companies and workers — mostly in tech — based on needs. As a result, he has a front row seat to the granularity that inevitably comes from individual lives and experiences. Those lives can be a bigger influence on expectations and needs than age. 

There might be a Boomer who looks after their grandchildren and has more in common with the Millennial colleague raising a child. That can change priorities around working from home or salaries. 

All of those experiences and expectations can form a workplace and shift a culture, bringing a range of knowledge and problem solving to a situation. 

Just don’t chalk it up to age alone. 

“Unfortunately, it’s not that simple,” says Wawruck. “‘Oh, you’re born between this year and this year? Now, I know you and I know everything about you and I can categorize you easily.’ I wish it was that easy.”

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Burnout at work: how to reset yourself

If you’ve ever felt completely deflated, demoralized, or “mentally spent” at work — or as an entrepreneur — you might take some comfort in knowing that you are far from alone.



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If you’ve ever felt completely deflated, demoralized, or “mentally spent” at work, you might take some comfort in knowing that you are far from alone.

In March of this year, CNBC reported that burnout at work is on the rise. Of 10,000 workers polled in the US and UK, 40% said they are burnt out — up two percent from previous years. Respondents say it’s due to pressure to achieve, or the threat of downsizing that’s causing anxiety.

And we’re not just talking about those who have had to return to offices (or have never left).

In December 2022, Travel Perk reported that about half of employees working from home say that they lack emotional support, and 86% experience high levels of exhaustion. Factors leading to this included the inability to disconnect from work, unfulfilling work, and lacking a means to address burnout.

What are the signs of burnout? How can employers help?

Ed Schild, CEO of Regesh Family and Child Services, an organization whose focus is on clinical treatment of youth and families, advised to watch for the red flags of burnout: “The day has just started and they are already tired. And they are finding they have less patience than they used to have. They might be getting grumpy with coworkers. They might be talking with coworkers secretly about their feelings, so neither of them are getting the help they need. That doesn’t help either,” he said. 

Photo courtesy Ed Schild

“So, the first thing, foremost, is that you need someone to talk to in a safe discussion. You might be embarrassed to tell the boss why you need the time off, as it seems like an excuse to take time off. The fact is, you need it for yourself, the company, and the clients. If we are burned out, we are not going to do a good job.” 

Thought leader and author David Burkus noted that, in his estimation, burnout can lead to decreased productivity, increased absenteeism, and even physical and mental health issues.

“By empowering employees and giving them a sense of control over their work, leaders can help prevent burnout and increase job satisfaction,” he advised.

His insights on leadership have been featured in major mainstream media, and he has been tapped by the likes of PepsiCo, Fidelity, Adobe, and NASA. He has recently written articles on the topic, looking at What Causes Burnout At Work, and How to Avoid Burnout At Work.

Photo courtesy David Burkus

In terms of avoiding toxic work environments, his advice is for managers to create “a positive and inclusive work culture where everyone feels valued and supported, (that) can help prevent burnout and foster a more harmonious work environment.”

Mental preparedness must begin before the work day, recommended Mordechai Rothman, Executive Director of Chai Lifeline Canada, an organization that provides a myriad of initiatives and emotional support to sick kids, their siblings, and parents.

“Review your schedule just before you start your day, so that you know what to expect, and can deal with whatever comes up. Give yourself a ‘warning order’ to subconsciously prepare your brain for what situations and discussions you will need to have during the day. Always try to leave 10 minutes between meetings to debrief and decompress your mind.”

Mordechai Rothman (photo by Jaskaran Singh)

He also suggests engaging in conversations with colleagues on topics other than shop talk, as this offers a human element to the work environment. Moreover, he advocates finding a silver lining to the workday.

“Every job has a meaningful side to it – it’s critical to focus on that. Whether you’re helping people file their taxes or pressing a button on a machine all day, there is always a bigger picture,” he explains. “What joy or happiness are you bringing to others through your job?… This helps ensure that when you get down, or stuck in mundane details, you are able to focus on the higher purpose your job brings to the world, which in turn will ultimately add more joy to your own life.”

Entrepreneurship and burnout

Neil Seeman’s newly-released book — Accelerated Minds: Unlocking the Fascinating, Inspiring, and Often Destructive Impulses that Drive the Entrepreneurial Brain — reviews some of the challenges of office burnout for entrepreneurs.

De-stigmatizing the discussion of mental overload is a first good step, he said. “The more the CEO and leader talks about it, it enables other people to talk about it. The employee really needs to feel comfortable talking with their manager about what they are going through. You can’t hack mental health. You can’t hack it with benefits and online training. Because it has to come from the top.” 

“I think it comes down to hiring and training good managers for situational or authentic leadership,” noted Seeman, who teaches at University of Toronto’s Dalla Lana School of Public Health. 

Photo courtesy Neil Seeman

Dialog about mental health should also extend to the home and among relatives.

“I talked (in the book) about the importance of being transparent with your significant other or family about both financial and emotional health challenges you might endure in the (entrepreneurial) journey. If and when things go off the rails, or even if they are tremendously successful, you want to have that transparent discussion. Entrepreneurship is more than just the one person – it’s the family unit.” 

In the book, Seeman covers the tragedies of what happens when entrepreneurs do not see, or do not handle, mental burnout: Twice as high rate of hospitalization for suicide, three times higher rates of substance abuse and addiction, and a lifetime prevalence rate of one mental health challenge.

“That’s why I talk a lot toward the end of the book about really preparing the next generation of entrepreneurs for the journey. The messaging has to be a lot clearer. It has to convey not just the glorious upside, but also the downside,” he added. 

“You need a peer group of other entrepreneurs, a real coach, to share these challenges with.” 

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