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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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DX survey reveals high levels of enterprise-consumer disconnect

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A new survey looks at the global investment and effectiveness of businesses’ digital transformation efforts. The survey shows a disconnect between enterprise investments and consumer experiences.

The survey is titled “The Kony Digital Experience Index (KDXi) Survey”, and the main takeaway is that while businesses have invested nearly $5 trillion on digital transformation initiatives, only 19 percent of customers have reported any significant improvement in the experiences offered to them.

The Kony Inc., survey included 1,600 responses from business leaders and customers across the U.S., Europe and Asia. The responses were used to gauge the target digital project implementation efficiencies in banking, retail, utilities and healthcare. The research showed a disconnect on both sides and a potential misalignment around investment priorities, and highlighted the impact this could potentially have for businesses.

Among other things, the study found that consumers are underestimating the number of businesses that are investing heavily in every customer experience outcome by at least 50 percent. This means that while business are spending money on digital transformation projects, consumers are not necessarily noticing a difference.

The survey also reported that 62 percent of consumers say that they spend more with companies that offer effortless digital experiences, while 56 percent of consumers indicate that they will switch if a retailer does not deliver the digital experience they want. This signals the necessity for businesses to continue to invest in the digital experience for the customer. However, in doing so they need to start making an impact.

As the report states: “It is critical for businesses to have a greater focus on understanding and aligning with customer needs and priorities to ensure that they are driving the agenda for the digital technology they create and fund.”

In terms of what businesses should be doing, the basis of a strategy includes:

  • Embracing innovative thinking, ambition and a commitment to improvement
  • Prioritizing investment in digital outcomes, not digital initiatives
  • Getting their foundations right before evolving
  • Building for now, but investing in a roadmap that leads to the future
  • Saying no to silos and yes to integrated digital strategy
  • Setting a customer-centered digital transformation agenda

This means companies should work to provide web experiences that make it easier for users to navigate, and for websites to be more engaging and intuitive to use. There also needs to be comprehensive online and mobile facilities so that users can do everything online or via their mobile device. Furthermore, to truly step forwards, businesses need to begin offering digital experiences such as AI, chatbots and augmented reality.

Summing this up, Thomas E. Hogan, chairman and CEO, Kony, Inc. states: “Improvements in costs and efficiencies are always welcomed and clearly important to project funding, but the real returns and real impact of digital starts and stops with its impact on the customer experience.”

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‘Ethical AI’ matters — the problem lies in defining it

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News that Microsoft will invest around $1 billion to examine ethical artificial intelligence signals that the tech sector is thinking deeper about the ethics underlying transformative technologies. But what is ethical AI?

Microsoft is to invest around $1 billion into the OpenAI project, a group that has Elon Musk and Amazon as members. The partners are seeking to establish “shared principles on ethics and trust”. The project is considering two streams: cognitive science, which is linked to psychology and considers the similarities between artificial intelligence and human intelligence; and machine intelligence, which is less concerned with how similar machines are to humans, and instead is focused on how systems behave in an intelligent way.

With the growth of smart technology comes an increased reliance for humanity to place trust in algorithms, that continue to evolve. Increasingly, people are asking whether an ethical framework is needed in response. It would appear so, with some machines now carrying out specific tasks more effectively than humans can. This leads to the questions ‘what is ethical AI?’ and ‘who should develop ethics and regulate them?’

AI’s ethical dilemmas

We’re already seeing examples of what can go wrong when artificial intelligence is granted too much autonomy.Amazon had to pull an artificial intelligence operated recruiting tool after it was found to be biased against female applicants. A different form of bias was associated with a recidivism machine learning-run assessment tool that was biased against black defendants. The U.S. Department of Housing and Urban Development has recently sued Facebook due to its advertising algorithms, which allow advertisers to discriminate based on characteristics such as gender and race. For similar reasons Google opted not to renew its artificial intelligence contract with the U.S. Department of Defense for undisclosed ethical concerns.

These examples outline why, at the early stages, AI produces ethical dilemmas and perhaps why some level of control is required.

Designing AI ethics

Ethics is an important design consideration as artificial intelligence technology progresses. This philosophical inquiry extends from how humanity wants AI to make decisions and with which types of decisions. This is especially important where the is potential danger (as with many autonomous car driving scenarios); and extends to a more dystopian future where AI could replace human decision-making at work and at home. In-between, one notable experiment detailed what might happen if an artificially intelligent chatbot became virulently racist, a study intended to highlights the challenges humanity might face if machines ever become super intelligent.

While there is agreement that AI needs an ethical framework, what should this framework contain? There appears to be little consensus over the definition of ethical and trustworthy AI. A starting point is in the European Union document titled “Ethics Guidelines for Trustworthy AI“. With this brief, the key criteria are for AI to be democratic, to contribute to an equitable society, to support human agency, to foster fundamental rights, and to ensure that human oversight remains in place.

These are important concerns for a liberal democracy. But how do these principles stack up with threats to the autonomy of humans, as with AI that interacts and seeks to influencing behavior, as with the Facebook Cambridge Analytica issue? Even with Google search results, the output, which is controlled by an algorithm, can have a significant influence on the behavior of users.

Furthermore, should AI be used as a weapon? If robots become sophisticated enough (and it can be proven they can ‘reason’), should they be given rights akin to a human? The questions of ethics runs very deep.

OpenAI’s aims

It is grappling with some of these issues that led to the formation of OpenAI. According to Smart2Zero, OpenAI’s primary goal is to ensure that artificial intelligence can be deployed in a way that is both safe and secure, in order that the economic benefits can be widely distributed through society. Notably this does not capture all of the European Union goals, such as how democratic principles will be protected or how human autonomy will be kept central to any AI application.

As a consequence of Microsoft joining of the consortium, OpenAI will seek to develop advanced AI models built upon Microsoft’s Azure cloud computing platform. There are few specific details of how the project will progress.

Commenting on Microsoft’s big investment and commitment to the project, Microsoft chief executive Satya Nadella does not shed much light: “AI is one of the most transformative technologies of our time and has the potential to help solve many of our world’s most pressing challenges…our ambition is to democratize AI.”

Do we need regulation?

It is probable that the OpenAI project will place business first, and it will no doubt seek to reduce areas of bias. This in itself is key to the goals of the partners involved. For wider ethical issues it will be down to governments and academia to develop strong frameworks, and for these to gain public acceptance, and then for an appropriate regulatory structure to be put in place.

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Digital transformation is causing C-suite tensions

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Digital transformation is not only about technology, it’s also about changes of practices which need to diffuse through an organization’s culture. This needs to be begin at the top. A new report finds C-suite discord is a block to effective DX processes.

Rapidly undergoing effective digitally transformation puts a strain across C-suite relationships, according to a new survey of major enterprises. The report has been produced by business management software provider Apptio, and commissioned by the Financial Times. Titled “Disruption in the C-suite“, the report is draws on the findings of a survey conducted with 555 senior executives, (50 percent occupying CxO roles). The executives were based in major economic nations: Australia, Denmark, France, Germany, Italy, Japan, the Netherlands, Norway, Spain, Sweden, the UK and the U.S.

The report finds that while digital transformation leads to greater collaboration across different business functions, it can also create blurred responsibilities across the C-suite. This crossover carries the risk of key issues being missed; it also serves as a source of tension between top executives, as traditional functions merge and territorial disputes are triggered. As a sign of such differences, 71 percent of finance executives found the IT unit within the C-suite should be seeking greater influencing skills to better deliver the change their business requires.

Team deficiencies found in the survey included not having key performance indicators in place with to measure digital transformation progress. Also, the CFO was found to be the least deeply aligned member of the C-suite team, especially not being aligned with the CIO.

To overcome these divisions, the report recommends that organizations invest time in ‘bridging the trust gap’ between functions and seek to ease tensions, especially between the offices of the CIO and the CFO. An important factor is with establishing which function has accountability. Another measure that can be taken is with ensuing that data is more transparent and where key metrics are issued in ‘real-time’.

The report also charts how digital transformation is being fully embraced, as leaders at global brands are embracing processes and technologies like artificial intelligence, workplace reskilling, cloud computing, agile working and de-centralized decision-making.

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