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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.

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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 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.

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U.S. proposes redefining when gig workers are employees

U.S. labor officials proposed a rule change that could make it easier for gig workers to be entitled to benefits.

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A rule change proposed by US labor officials that could make it easier for contract workers to be reclassified as employees shook investor confidence in the future of "gig economy" firms such as Uber and Lyft
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United States labor officials proposed a rule change Tuesday that could make it easier for gig workers such as Uber drivers to be reclassified as employees entitled to benefits.

The move by President Joe Biden’s Labor Department would lower a bar set by his predecessor regarding when someone is considered an employee instead of a contract worker.

It also comes as “gig economy” companies from rideshare platforms to food delivery services strive to maintain the status quo.

The new formula includes factors such as how long a person works for a company and the degree of control over the worker, as well as whether what they do is “integral” to a business, according to the proposed rule.

“We believe the proposed regulation would better protect workers from misclassification while at the same time providing a consistent approach for those businesses that engage or wish to engage with independent contractors,” Jessica Looman of the US Department of Labor said at a press briefing.

Being classified as employees would entitle workers to sick leave, overtime, medical coverage and other benefits, driving up costs for companies such as Uber, Lyft and DoorDash that rely on gig workers.

The proposed rule change is subject to a 45-day public comment period, meaning there is no immediate impact, but share prices took a hit on the news.

Uber and Lyft shares ended the formal day down more than 10 percent, while DoorDash was down nearly six percent.

“It’s a clear blow to the gig economy and a near-term concern for the likes of Uber and Lyft,” despite uncertainty about how the new rule might be interpreted across the country, Wedbush analyst Dan Ives said in a note to investors.

“With ride sharing and other gig economy players depending on the contractor business model, a classification to employees would essentially throw the business model upside down and cause some major structural changes if this holds.”

Uber and Lyft have consistently argued that their drivers want independence, provided benefits are added to the mix.

In California, the cradle of the gig economy, voters in late 2020 approved a referendum backed by firms such as Uber that preserved keeping drivers classified as independent contractors.

The measure effectively overturned a state law that would require the ride-hailing firms and others to reclassify their drivers and provide employee benefits.

The vote came after a contentious campaign with labor groups claiming the initiative would erode worker rights and benefits, and with backers arguing for a new, flexible economic model.

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How can organizations attract and retain IT talent?

Gartner has outlined three ways

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One of the biggest stories in digital transformation right now? Attracting and retaining IT talent. 

According to Gartner, the labor market has tightened in the last two years. They report that:

  • 60% of HR leaders are “significantly concerned” about employee turnover.
  • 62% of candidates have explored a career change in the last year.
  • Nearly three-quarters of candidates who receive a job offer have at least one other offer on the table.

Amid stories from the ‘Great Resignation,’ workers in all industries are pushing for higher compensation, better benefits, and increased flexibility — and IT talent is no exception. In fact, Gartner’s Global Labor Market Survey found that compensation is the top driver for IT talent attraction and retention. According to a recent Gartner IT Compensation Increase Poll, 50% of organizations reported increasing the salaries of key employees after they received a separate job offer — all in a bid to retain this talent.

How can organizations effectively attract talent and, most importantly, retain these employees? Gartner has outlined three ways.

Make monitoring and raising pay competitiveness a priority

As Gartner explains, “In order to pinpoint where additional funding will be necessary to address pay gaps in the short term, work with your HR team to identify IT roles and skills areas facing higher attrition risk and recruitment challenges due to noncompetitive compensation.”

Limited resources? Prioritize roles in high-risk areas, they explain.

Build flexibility into IT compensation through variable pay programs

“One way to minimize locking in compensation adjustments as long-term fixed costs,” explains  Lily Mok, Gartner VP Analyst, “is to use variable pay components that can be adjusted or removed as talent needs and market conditions evolve.”

Examples of these include skills-based premium pay, a signing bonus (lump sum or split up), and retention bonuses (eg. during a major period of transition).

Make sure managers can have successful pay-related conversations

According to Gartner, there are three important elements needed to make sure these conversations are effective. 

First, never forget empathy — especially since finances are a very personal topic and can be a sensitive issue.

Second, make sure the compensation package’s value is clearly outlined and understood. This includes pay, bonuses, benefits, etc.

Finally, be transparent about the organization’s pay structure, and how pay rates are set. After all, there are many sites out there (eg. Glassdoor) that features self-reported public pay data. 

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How will CIOs define success in 2021?

New research suggests CIOs are prioritizing digital transformation to “future-proof” their organizations and build resiliency.

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Recently, we reported IDC’s 2021 predictions, which noted that while CIOs have faced epic-level challenges this year, they’ll need to be in the front seat of the upcoming economic relief efforts.

At the top of IDC’s list was the prediction that by 2022, “65% of CIOs will digitally empower and enable front-line workers with data, AI, and security to extend their productivity, adaptability, and decision-making in the face of rapid changes.”

Since then, Gartner has also chimed into the CIO + Future of Work discussion. They identified “automation of routine work with AI, digital dexterity, and hybrid work with distributed workforce” as areas CIOs should focus on.

Now, a new report (based on a survey of over 100 Fortune 500 CIOs) from digital adoption platform WalkMe has uncovered how CIOs and IT organizations will define success in 2021, expanding on these aforementioned trends.

Multi-pronged approaches

In The CIO Outlook 2021, WalkMe — who commissioned Constellation Research for the report — found that 77% of CIOs list automation and AI as key to improving the effectiveness of IT. 59% say ROI from IT can be achieved through portfolio assessment and rationalization.

“CIOs are prioritizing overall digital change, keeping the organization safe, and improving the worker condition,” says WalkMe. Looking ahead, “CIOs must invest in finding the right models for enabling remote work while supporting their users.”

In order for organizations to adapt to change and become future-proof, CIOs need a multi-pronged approach, featuring:

  • No-code solutions
  • The automation of repetitive processes
  • Key software integration
  • Training and service through new approaches

As quoted in ITProPortal, Constellation VP and Principal Analyst Dion Hinchcliffe says:

“This data, gathered from top CIOs around the world, shows that they will be seeking dramatic improvements, especially significantly higher ROI (10-20 percent+) from their IT investment next year.” 

Want to read the full report? Find it here.

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