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#ScaleStrategy: Growing sales from one to many

How Nudge.ai CEO and co-founder Paul Teshima is using hard-earned lessons from the past to transform his startup sales team into a scaling one.

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Steve Woods, Paul Teshima
Nudge.ai was co-founded in 2014 by former Eloqua executives, Steve Woods (left) and Paul Teshima
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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.  Read the in-depth Q&A with Teshima here.

“One of the most important aspects of scaleups is figuring out how to transition sales – from a founder to a larger sales team. It’s also one of the hardest,” says Paul Teshima, CEO and co-founder of Nudge.ai, a relationship intelligence platform that helps sales teams to access new accounts, analyze deal risk, and measure account health.

And, he knows what he’s talking about.

Teshima is a Canadian-born serial entrepreneur and a rare breed too. His previous company, Eloqua, achieved unicorn status.

As part of Eloqua’s executive team, Teshima grew the company to more than $100 million in revenue over 13 years, through two economic crises, its IPO and its eventual acquisition by Oracle for US$957 million in 2012.

Today, from Nudge.ai’s office in OneEleven, Teshima and his co-founder Steve Woods (also a co-founder at Eloqua), are hoping to scale up again. Since launching in 2014, the company has grown to 22 employees, several major enterprise clients and over 20,000 B2B users on the platform. And they were recently featured in the Wall Street Journal on how AI is changing sales. It’s no surprise they’re gaining momentum given the growing need for digital relationship management support. After all, Google, Salesforce, Microsoft, Cisco, and more tech giants are moving into the space.

As Nudge.ai builds out a sales team, Teshima is leaning on lessons from his past and learning new ones about who, how and when to hire, what founders forget about when training newbies, and the art of cracking an enterprise deal. 

From One to Many

When it comes to the first few sales hires, Teshima believes they should be entrepreneurial. His approach to building a high-performance sales team is what he calls a classic best practice: hire people in pairs so that you can start removing variables. For example, if both salespeople are having trouble, it may mean that it’s not the right time to transition. If one is successful and the other is not, then it could mean you didn’t hire someone with the right skills.

Nudge.ai is in the process of transitioning its founder-oriented sales team to a larger group. “We’ve got some salespeople working on that delicate transition period now,” he says. “I can tell you that I’m already overestimating how much I think they know because I take my knowledge for granted. I mean, of course they don’t know what I know, it’s in my brain still.”

As a company scales, Teshima urges founders to pause and appreciate how much they know about the business, and how quickly they can make decisions at the drop of a hat in a deal cycle. Those skills are not always things salespeople can do right away.

“It’s really important to simplify,” he says. “Understand what can be translated to a salesperson that he or she can then repeat over and over again.”

To support their success, Teshima focuses on being as methodical as possible throughout on-boarding and training. In addition, he brought someone in to help simplify the sales process to determine what can be scalable.  

Hiring Sales People

Should you hire a Director of Sales or build the team from the bottom up? Teshima says it depends on where you sit on the revenue curve as well as the capital and talent that’s available to you at the time.

He definitely sees the value of of hiring a Director of Sales first who can “carry the bag” and help to scale that initial phase, but also agrees with the approach of hiring a hands-off VP to go build up the entire team.

“Both require early evidence of some form of scale. You have some sort of process that defines how the sales process works today and also key metrics about it,” he says.

Teshima acknowledges that finding sales talent can be a challenge. “Are there less seasoned salespeople in Canada who have gone from $0 to $100 million than in the Valley? Yes. Do we need to solve that problem? Absolutely. But you are seeing a lot of seasoned people coming back and as that continues you’re going to see those people train others to get to the next scaling point,” he says.

Closing Enterprise Deals

Enterprise deals are coveted targets for scaleups for the revenue, for the credibility, and for the learning that they offer.

“The hardest part of closing an enterprise deal is finding it,” says Teshima. “Getting involved in the sales cycle itself is challenging because decision-makers are so inundated with a barrage of outbound outreach. These buyers shut down and avoid dealing with 20 or 30 vendors.”

He says that if you’re going to play in the enterprise space, you should understand what you’re getting into. First, it’s difficult to get in. Secondarily, startups can’t wait out a 44-month sales cycle knowing the deal may not close. “You can, but you’ll be losing a lot of sleep,” he says.

Teshima’s scaleup strategy is to show pocketed value right out of the gate. “Lock them in and then go from division to division quickly. And do it more cost-effectively than the competitor. Try that approach versus just the top down approach.”

When it comes to offering freebies or deals to close a deal quickly, Teshima believes low-paid pilots can be risky.

“Enterprises today actually have slush funds to experiment with technology where they didn’t before,” he says. “You could be in a small little pilot where they throw money at you and you wouldn’t even know if it’s a real deal or if they’re throwing real resources behind it. It is absolutely true that if they put some skin in the game, you’ll have a more successful pilot. You need to be pretty disciplined about qualifying, and if you invest in the cycles then put a price on it.”

What about when enterprise customers who scaleback during the renewal process?

Teshima says he hasn’t experienced this yet at Nudge.ai, but in the 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 existing customers. You should never forget that customers can always come back and champions can always move jobs. You always want to do right in those situations because you never know when you’re going meet them next in the ecosystem,” he says.

Channel Partners Sales

In B2B sales, channel partners can be a tempting avenue to explore. While there are good synergies on the tech side – on the cloud and services side – it can be more challenging to have channel partners depending on the nature of the product, says Teshima. In fact, he warns against channel partners in the early scaling stage.

“If you think training your first salesperson is hard, try training channel partners on your product when they have 20 competing products to sell and they’re making a small margin on your product,” he says. “You can get lucky and find one strategic partner and go big, but more often than not, you’re going to find that they’ll get all excited, get trained, and not sell anything. Even if they do close something, it may not even be the right fit,” he says.

Instead, Teshima recommends, clearly establishing that you can directly sell your product in a repeated way before you think about channel partners.

Scaling a sales team isn’t easy. And it won’t happen overnight.

“My one piece of advice is that it’s never one thing,” he says. “It’s a million little things you need to do every day. That’ll make you more successful than trying to figure out the one thing that will help you hit the jackpot.”

Want more? Read the in-depth Q&A with Paul Teshima for more insights on scaling sales. 

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Americans' pandemic-era entrepreneurial streak is holding strong—for now

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An altLINE analysis of Census Bureau data reveals Americans are still starting new businesses at higher rates than in pre-pandemic times.
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Inflation has nothing on the American entrepreneurial spirit, which, judging by the volume of new businesses formed, continues to see potential in the post-pandemic economy.

To better understand the post-COVID-19 outlook for entrepreneurship in the U.S., altLINE analyzed data and reports from the National Bureau of Economic Research and the Census Bureau. The data shows that Americans are on track through July of this year to submit 54% more applications to start new businesses compared to the same period in 2019, before the onset of the pandemic.

New business applications soared initially at the start of the COVID-19 pandemic as brick-and-mortar businesses were forced to close their doors in compliance with local social distancing mandates. Stores saw business plummet and many were never able to reopen their doors, even as public health restrictions eased. The seismic shift in shopping habits spurred many Americans to start new business ventures at rates not seen since before the Great Recession, when the U.S. consumer took a hit from one of the deepest recessions on record.

As the current economic situation puzzles economists who debate whether a recession may be in the future, the continuing creation of businesses could mitigate some of the pain of a slowing economy.

Studies have suggested that the growth of the smallest businesses can help an economy’s resilience. Young, tiny companies, sometimes called “microbusinesses,” reduce local unemployment rates in their communities and have been related to rising household incomes, according to GoDaddy’s July 2021 Venture Forward Report.


A line chart depicting business formation applications submitted every month from 2019-2023. The trend line spikes in 2020, comes down slightly and then continues growing slowly in 2023.

altLINE

COVID-19 recession provides shot in the arm

Advancements in technology made it easier for business owners to set up and run online storefronts and services. Leading up to 2020, ecommerce platforms integrating new technology for enhanced shopper experiences provided a critical foundation for the spike in new businesses. As Americans stayed at home during the height of the pandemic, they shopped online for everything from personal care to groceries. Ecommerce sales nearly doubled in 2020, jumping by 43% to a whopping $815 billion in annual retail sales. Thousands in stimulus checks also did their part to keep Americans afloat—and spending. On top of those factors, interest rates for loans to buoy new companies and purchase real estate were at historic lows.

In the first year of the new business surge, retailers in the fashion space made up the lion’s share of new small businesses, according to the GoDaddy Venture Forward Report.

Today, those new business owners face a much more expensive economy. Costs for labor, gas, clothing, food, and other critical inputs for businesses have risen considerably since 2020.

Business owner using mobile app on smartphone checking a parcel box.

Ground Picture // Shutterstock

New business class faces considerable headwinds

The typical new business faces its most difficult time in its first years of operation. Historically, 4 in 5 new businesses make it beyond their first year, according to Bureau of Labor Statistics data. But the odds of survival dwindle in each subsequent year of operation. Based on trends, just 1 in 2 businesses created in 2020 will likely survive beyond 2025.

The entrepreneurs looking to survive now face mounting headwinds in the face of rising interest rates, which has made borrowing money more expensive for both consumers and small business owners.

For small businesses seeking venture funding, seed-stage venture capital has stagnated as the venture capitalist ranks have grown wary of investing in early-stage companies. For those seeking loans, the cost of borrowing money today is at its highest since 2001, when the tech bubble burst, throwing the U.S. into recession.

Story editing by Ashleigh Graf. Copy editing by Kristen Wegrzyn.

This story originally appeared on altLINE and was produced and
distributed in partnership with Stacker Studio.

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Robots are starting to deliver takeout orders. Are they here to stay?

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Task Group analyzed the state of autonomous delivery systems, both nationally and internationally, to see how far along this technology has come.  
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In a March 2023 Deloitte survey, 47% of Americans said they would order from a restaurant that delivers food with a drone or an autonomous vehicle. That’s up 3 percentage points from the company’s 2021 survey about restaurant trends.

In that first survey, researchers noted there was “massive uncertainty in the industry, and many worried that restaurant patronage might never recover” from the COVID-19 pandemic. It found that two-thirds of consumers believed they would not immediately return to their pre-pandemic restaurant habits.

In 2023, most restaurant customer behavior is back to normal—though some changes have blended into the industry’s practices. Task Group analyzed the state of autonomous delivery systems, both nationally and internationally, to measure the progress of this technology post-pandemic.

As with other industries, technology has helped maximize efficiency and improve customer satisfaction. Business owners learned new service methods, marketing strategies, and technical terminology. Food delivery skyrocketed during lockdowns, making greater strides in restaurant efficiency and, in some cases, profits. Many restaurant owners connected apps that allowed customers to order without talking to a human to state-of-the-art delivery systems that don’t require a driver.

Restaurants and transportation companies in North America and Europe are experimenting with new automated delivery techniques that can reduce their costs as long as they do not compromise customer satisfaction. And consumers are ready—but how soon will it become standard practice?


Food delivery robots on pathway.

Julija Sh // Shutterstock

What are drones and sidewalk delivery vehicles?

The robots most commonly used in the food delivery industry are aerial drones and wheeled autonomous delivery vehicles that travel along sidewalks to reach customers.

Drones are classified by how they generate lift—with fixed wings, rotors, or a combination—by how they’re used, such as food delivery, and what equipment they have on board, including batteries and cameras.

In the U.S., the Federal Aviation Administration regulates drone use. The agency requires pilots to be certified—and bans drones within five miles of airports.

For many years, the FAA stood in the way of companies seeking to use drones for deliveries, but in 2019, the agency agreed to allow uncrewed delivery flights beyond the pilot’s line-of-sight by UPS and Wing Aviation, owned and operated by Google’s mothership Alphabet. Since then, the agency has approved drone delivery operations for several companies, including Amazon and Walmart.

According to a study published by the Harvard Kennedy School in 2022, autonomous delivery vehicles are not the future. They’re already here. Self-driving machines about the size of a large cooler are already traveling down our sidewalks and crosswalks to deliver various packages.

Policymakers question how these vehicles will work and interact with people and other vehicles in already congested and chaotic urban environments. The Harvard researchers believe these vehicles “offer the promise of less congestion and greener shipments,” but also “raise concerns about safety and use of road and sidewalk infrastructure.”

While the debate continues, the manufacturers of these robots continue to advance their technology, including using machine learning to improve navigation, efficiency, and safety.

Food delivery drone in flight.

Canva

How far off are drone or sidewalk deliveries?

Estonia-based delivery startup Bolt, working with Starship Technologies, has been trialing sidewalk deliveries in Estonia, the U.K., and the U.S. and plans to formally launch robot deliveries later this year in as many as 500 cities in 45 countries.

Bolt’s main competitor, Uber, signed a deal in 2022 with autonomous vehicle startup Nuro “to test driverless food deliveries” in Mountain View, California, and Houston, Texas. Before the agreement, Uber ran a pilot program for sidewalk delivery in Los Angeles, while Nuro delivered Domino’s pizzas in specific areas of Houston for a year. 

Story editing by Jeff Inglis. Copy editing by Kristen Wegrzyn.

This story originally appeared on Task Group and was produced and
distributed in partnership with Stacker Studio.

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AI “superusers” seek education, fun, and productivity with generative AI

A look at two separate studies by Sparktoro and Salesforce on people’s generative AI use.

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Maybe it was through your job. Or simply out of curiosity.

With the rise of generative AI, you’ve probably tried out ChatGPT or a similar tool. But how often are people using these? More interestingly, what motivates them? Both Salesforce and SparkToro sought to find out with two separate studies. 

Here are highlights from each report and how they compare:

Work automation and educational pursuits top priorities for AI users

Both Salesforce and SparkToro can agree on this. SparkToro highlighted professional use of the platform as at an “all-time high,” then ranked categories of interest across over 4,000 ChatGPT prompts with these in the top 5:

  • Programming: 29.14%
  • Education: 23.30%
  • Content: 20.79%
  • Sales and Marketing: 13.47%
  • Personal & Other: 6.73%

Salesforce found that 75% of generative AI users are motivated by streamlined work communications and task automation. The second highest topic of interest? Technically “messing around” (38%), though a close third was learning and education (34%). Both SparkToro and Salesforce posit that education doesn’t just include homework or university coursework—users also use tools like ChatGPT to develop knowledge of other desired educational topics. 

Younger generations more likely to use AI than older ones despite general decline in usage

Salesforce surveyed 4,000 people to find out how they use generative AI and what their demographics are. Turns out, most “superusers” — aka those who use the tool every day — are Millennials or Gen Zers (65%). Plus, 70% of the Gen Z participants surveyed said they use generative AI. 

Still, SparkToro notes an overall decline in generative AI use regardless of age. After studying monthly traffic data on OpenAI provided by Datos, SparkToro found overall traffic fell by nearly 30%. 

Users ask ChatGPT to write, create, and list

These were the top three common words in SparkToro’s assessment in ChatGPT prompts. However, they also share a notable prevalence of the words “game” and “SEO in prompts as well. Other words less commonly used yet enough to come up in the results included judge, SaaS pricing, curriculum, employment, and employer.

Read the SparkToro report here and the Salesforce report here

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