Q&A: Paul Teshima, CEO & Co-founder, Nudge.ai, 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.
#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 Nudge.ai, 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 Nudge.ai, 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 Nudge.ai 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 Nudge.ai 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 Nudge.ai. 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.
#ScaleStrategy is produced by DX Journal and OneEleven. This editorial series delivers insights, advice, and practical recommendations to innovative and disruptive entrepreneurs and intrapreneurs.
Rising costs, work-life balance among top mental health stressors for Canadian entrepreneurs
A look at BDC’s latest survey results on mental health challenges for Canadian entrepreneurs.
Have you recently gone into business for yourself? BDC’s latest survey indicates a higher likelihood of you facing some mental health challenges.
And you’re more likely to seek professional help if you’re a:
- Younger business owner
- Business owner with 20+ employees
- Business owner in the arts, entertainment, and recreation fields
- Startup business owner
While men and older business owners were less likely to seek professional health, that doesn’t necessarily equal fewer mental health challenges.
Indeed, BDC’s latest survey on 1,500 Canadian SME business owners and mental health illuminates a concerning 45% increase in Canadian business owners facing mental health challenges (compared to 38% last year).
Here are some more highlights from the report:
More Canadian entrepreneurs feel tired and depressed, with fewer seeking help
The survey responses show that 67% of entrepreneurs felt tired and low-energy at least once a week. Similarly, nearly 50% felt depressed and like they didn’t accomplish everything they would have liked to.
“Entrepreneurs often comment that it feels lonely at the top and rarely speak candidly about organizational and personal challenges,” said Hassel Aviles, co-founder of Not 9 to 5.
While certain groups are more likely to seek support than others, the survey still only shows about a third (35%) of respondents actually sought mental health support.
And the hesitation isn’t a matter of pride. The top barrier to seeking help was the high costs of mental health services, with uncertainty and discomfort discussing things following close behind.
“I currently pay out-of-pocket for a private therapist,” said one anonymous survey respondent. “I am very grateful for that, and I click with my therapist well, but it typically costs me $200- $400 per month. This is a hard expense to tend to in the current economic situation.”
Inflation and work-life balance are top stressors
The survey showed that 54% of entrepreneurs cited inflation and work-life balance as top stressors. The two go hand-in-hand, since rising costs fuel longer hours to make ends meet. Notably, work-life balance was a more sought-after support to mitigate the stress, followed by better access to mental health resources.
“Inflation rates and other factors are affecting their businesses in ways that are harder to control, leaving many entrepreneurs resorting to working even longer hours just to stay afloat,” said Annie Marsolais, CMO at BDC.
Small business owners are just as mentally strained as medium business owners
You might assume these findings apply more to “bigger” business owners with 20+ employees. But the survey profile indicates that 88% of respondents have under 20 employees, with 56% having under five employees.
“As individuals, we can’t control the rates of inflation and the stress it may cause,” said Aviles. “But we can learn to manage our reactions to that stress. Learning how to do this is an opportunity to create separation between who we are and the work we do, which is healthy, and supports the work-life balance entrepreneurs are seeking to achieve.”
Read BDC’s full survey results.
Veronica Ott is a freelance writer and digital marketer with a specialization in finance and business. As a CPA with experience in the industry, she’s able to provide unique insight into various monetary, financial and economic topics. When Veronica isn’t writing, you can find her watching the latest films!
What are the primary reasons people in tech change jobs?
Tech is known to have a high degree of employee turnaround, with workers seeking better work-life balance, advancement opportunities, and pay.
It’s not unusual for the tech sector to experience a high degree of turnaround, as many employees are eager to walk away from dissatisfying work environments and burnout, according to ICONIC’s survey from last year.
But lately, there appears to be even more examples of workers jumping from company to company. Brenda Beckedorf, the executive director for Alberta IoT Association — a 200-member nonprofit that focuses on scale up tech companies — said that in the Wild Rose province alone, she’s familiar with a large number of tech workers in the past six months landing their third and fourth jobs.
Various reports and surveys show employees are lured by the promise of better flexibility, better pay, and better benefits — all increasingly important after the radical workshift during the pandemic. In certain instances, employees cite a want for professional development, or opportunities for advancement. Still for others, a new job that affords them work-life balance.
Further driving the point, a poll from December 2022 found that about one in seven Canadian employees at middle market and larger organizations report actively applying for jobs outside their current company. The reasons given range from the promise of better work-life balance, seeking more fulfilling work, and the potential for advancement, among other goals. The exodus is acutely felt by middle market businesses — nearly 70% of whom said they face staffing challenges.
In fact, Canada as a whole is facing challenges holding onto talented IT professionals. Whereas many migrate to other companies within the country, there is definitely a contingent who migrate to the US. They’ve told various pollsters it’s because of better pay and the prestige of working for a recognized brand such as Google, Alphabet, Apple, Microsoft, Intel, and others.
Indeed, there is a marked wage gap, providing a massive incentive. The average IT worker in Toronto rakes in $117K, in contrast to Silicon Valley ($196K), New York ($180K), and Seattle ($186K).
A study reported in the Globe and Mail, showed that two-thirds of Canadian software engineering graduates find work in the US — and end up staying there.
Half of Canadian workers will job hunt in 2023 because they’re seeking higher pay and perks, according to a poll by recruitment firm Robert Half.
The number of active job-seekers, in fact, was much lower just a year or so ago. In 2021, it was 21%; in 2022 it was 28%. After the tangibles of compensation, job-seekers also want a comfortable corporate culture, and good company values, according to the survey. In an article titled “Tech companies want workers, but it’s getting tougher to find them,” the Globe and Mail confirmed that, while “from fledgling startups to industry stalwarts – are firmly in expansion mode,” wages continue to lure staff away.
The secret to retention? Culture.
Given the bleed out of staff, the secret to retaining talent is “culture all the way,” Beckedorf said. “I really actually do believe that if people believe that they’re valuable, they feel like there’s a place for them to move up… When you take a chance on someone, invest in their potential, and treat them well, they’ll do the same for you.”
Furthermore, to mitigate employee losses, human resources might want to consider taking a new approach to hires.
As a sample paradigm: After a six month course, a would-be staffer might not have an impressive tech resume, but their decade as an engineer, for example, could be an asset. “And so giving time for those people and having a culture to say, ‘we’re going to train that person,’ I think that’s a big part of what we have to focus on,” Beckedorf said.
She added that companies are very much feeling the pressure to increase in-house training — hiring people to build out their own internal courses, with the recognition that otherwise, staff won’t reach the seniority they desire.
Another out-of-the-box solution to retention could be a little help from taxpayers, she added.
It’s common for small and medium businesses to lose staff to a better paying company, but one way to attract (and keep) star talent, she added, is for the government to step up to the plate and offer grants to assist in covering the cost of the hire. “They need to put their money on this expensive person that’s actually going to help them move the needle on the organization,” she said. “We really don’t have any support around that. And that’s where we need to start really having that conversation with government.”
The benefits of a diverse workforce
Still another idea to fix the retention problem comes from the World Economic Forum (WEF), who add what might be an unexpected twist.
Diversity of the workforce, they maintain, is good for corporate growth — i.e. higher revenue and innovation. They add how diversity fosters worker satisfaction, and by corollary, helps with retention.
Suffice it to say, human resources may be well served by ensuring that the hiring pool isn’t homogenous. And if that wasn’t reason enough, Forbes reports that companies with diverse crews do better financially.
Dave is a journalist whose work has appeared in more than 100 media outlets around the world, including BBC, National Post, Washington Times, Globe and Mail, New York Times, Baltimore Sun.
Advice from an award-winning mentor to young entrepreneurs
Craig Elias is passionate about advising students with big business aspirations.
Entrepreneurs who become successful at an earlier age can have a bigger impact on the economy, one expert told DX Journal.
But entrepreneurship also presents unique challenges for young people, who don’t have as much experience to draw from.
It’s why that expert, award-winning business advisor and global entrepreneur Craig Elias is passionate about mentoring students.
“The first time I became an entrepreneur, it was super hard, but I was super lucky that I had some amazing [work] experiences,” Elias said.
“But if you’re young, or a new Canadian, or if you’re a student, you don’t have that 15, 20 years of experience you can then throw at something, and be as lucky as I was.”
A top sales performer at every company he worked for, Elias’s first startup won the $1,000,000 prize in a global billion-dollar pitch competition, and was later twice named by Dow Jones as one of the 50 most promising companies in North America.
LinkedIn named him as one of its top 50 B2B sales experts in 2019, Forbes magazine named him one of the most social sales people on the planet, and he was named one of the “Calgarians We Love” by Avenue Magazine in 2021.
Today, Elias is the entrepreneur-in-residence at Bow Valley College in Calgary, where he conducted a 2019 study with student research assistant Issha Shah that suggested a first-time 23-year-old entrepreneur can have quite an impact: they’re likely to generate an almost $24 million increase in GDP and add nearly $14.5 million to local economies.
“It’s a bit like investing early, right?” Elias said.
However, Elias and Shah’s research also suggested that first-time entrepreneurs between the ages of 23 and 25 are also in need of the most support — and after experiencing a lot of success, Elias is paying it forward.
Through his role at the college, he taps into his years of experience and serves as a mentor to students hoping to become first-time entrepreneurs.
“I will tell you what I would do if I [were] you,” Elias said. “I’m really focused on giving people honest, candid, authentic feedback.”
In a conversation with DX Journal, he offered insight into traits of successful entrepreneurs, some of what he offers young people in mentoring sessions, and how mentorship is changing.
Useful traits in entrepreneurship
A useful thing for young entrepreneurs to understand, according to Elias, is that entrepreneurship can’t be taught.
“It’s learned,” he said. “[So] the question is, how do you help somebody learn?”
Curious people who are lifelong learners, coachable, and like to read tend to have advantages, he added.
A lack of prudence is also an asset — those who are willing to break the rules and do things differently are often rewarded in entrepreneurship.
And finally, you’re only as good as your network.
“The data says the number one predictor of success for an entrepreneur is how big is your network,” Elias said.
“[And] if you suck at networking, you simply just find a way to get better.”
The goals of a mentoring session
When it comes to a mentoring session, Elias says his first priority is finding out what the mentee wants to take away from it.
His second priority is finding a way to be helpful — and not necessarily nice — with that honest, candid, and authentic feedback of his.
Often, his goals include helping a mentee think about things they haven’t considered, and an example is helping them understand the difference between competitors and competition.
While competitors do very similar, or the same, things that an entrepreneur does, Elias says the competition is “all the different ways the same problem gets solved.”
“I say, ‘Okay, well if you want a jewelry store and I own a jewelry store, what do we compete against?’” Elias said.
“People say, ‘We compete against each other.’ And I’m like, no – you compete against all the other ways that someone could say to someone they love, ‘I love you’ or ‘I’m sorry for being an idiot.’”
It means that in actuality, a jewelry store owner is also competing against flowers, chocolate, perfume, cars, purses, shoes, pets, and trips, Elias says.
“So, helping them understand,” he said.
“They go, ‘Oh, no one does the exact same thing I do. We have no competition.’ You always have competition.”
Mentorship can also help foster diversity among entrepreneurs, Elias says, and one of his goals is to help facilitate that.
“How do we get more people that are not like me — stale, male, and pale — to [get] into the ecosystem?” Elias said.
It led him to establish a program that pairs successful people with mentees who share life experiences.
“It’s all about helping people understand that they belong.”
How mentoring has changed in the last five years
The pandemic changed the way we work, and Elias says it changed mentorship, too: young entrepreneurs no longer have to travel to sit down with someone they are hoping to learn from.
“Everybody’s so used to doing things virtually,” Elias said. “You don’t have to be in the same geography as the person you want to get some time with.”
Students have a unique advantage because people immediately understand why they’re asking for help, Elias said.
LinkedIn is also a place for easy introductions that he says is frequently used by senior executives.
And speaking of those executives, a lot of them have become more approachable, Elias says.
“I think because they got some help, they’re much more willing to give it back. Karma, you know,” he said.
“And for some people, the way they make a difference is by mentoring.”
DX Journal covers the impact of digital transformation (DX) initiatives worldwide across multiple industries.
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