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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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Import costs in these industries are keeping prices high

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Machinery Partner used Bureau of Labor Statistics data to identify the soaring import costs that have translated to higher costs for Americans.  
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Inflation has cooled substantially, but Americans are still feeling the strain of sky-high prices. Consumers have to spend more on the same products, from the grocery store to the gas pump, than ever before.

Increased import costs are part of the problem. The U.S. is the largest goods importer in the world, bringing in $3.2 trillion in 2022. Import costs rose dramatically in 2021 and 2022 due to shipping constraints, world events, and other supply chain interruptions and cost pressures. At the June 2022 peak, import costs for all commodities were up 18.6% compared to January 2020.

While import costs have since fallen most months—helping to lower inflation—they remain nearly 12% above what they were in 2020. And beginning in 2024, import costs began to rise again, with January seeing the highest one-month increase since March 2022.

Machinery Partner used Bureau of Labor Statistics data to identify the soaring import costs that have translated to higher costs for Americans. Imports in a few industries have had an outsized impact, helping drive some of the overall spikes. Crop production, primary metal manufacturing, petroleum and coal product manufacturing, and oil and gas extraction were the worst offenders, with costs for each industry remaining at least 20% above 2020.


A multiline chart showing the change in import costs in four major product industries.

Machinery Partner

Imports related to crops, oil, and metals are keeping costs up

At the mid-2022 peak, import costs related to oil, gas, petroleum, and coal products had the highest increases, doubling their pre-pandemic costs. Oil prices went up globally as leaders anticipated supply disruptions from the conflict in Ukraine. The U.S. and other allied countries put limits on Russian revenues from oil sales through a price cap of oil, gas, and coal from the country, which was enacted in 2022.

This activity around the world’s second-largest oil producer pushed prices up throughout the market and intensified fluctuations in crude oil prices. Previously, the U.S. had imported hundreds of thousands of oil barrels from Russia per day, making the country a leading source of U.S. oil. In turn, the ban affected costs in the U.S. beyond what occurred in the global economy.

Americans felt this at the pump—with gasoline prices surging 60% for consumers year-over-year in June 2022 and remaining elevated to this day—but also throughout the economy, as the entire supply chain has dealt with higher gas, oil, and coal prices.

Some of the pressure from petroleum and oil has shifted to new industries: crop production and primary metal manufacturing. In each of these sectors, import costs in January were up about 40% from 2020.

Primary metal manufacturing experienced record import price growth in 2021, which continued into early 2022. The subsequent monthly and yearly drops have not been substantial enough to bring costs down to pre-COVID levels. Bureau of Labor Statistics reporting shows that increasing alumina and aluminum production prices had the most significant influence on primary metal import prices. Aluminum is widely used in consumer products, from cars and parts to canned beverages, which in turn inflated rapidly.

Aluminum was in short supply in early 2022 after high energy costs—i.e., gas—led to production cuts in Europe, driving aluminum prices to a 13-year high. The U.S. also imposes tariffs on aluminum imports, which were implemented in 2018 to cut down on overcapacity and promote U.S. aluminum production. Suppliers, including Canada, Mexico, and European Union countries, have exemptions, but the tax still adds cost to imports.

U.S. agricultural imports have expanded in recent decades, with most products coming from Canada, Mexico, the EU, and South America. Common agricultural imports include fruits and vegetables—especially those that are tropical or out-of-season—as well as nuts, coffee, spices, and beverages. Turmoil with Russia was again a large contributor to cost increases in agricultural trade, alongside extreme weather events and disruptions in the supply chain. Americans felt these price hikes directly at the grocery store.

The U.S. imports significantly more than it exports, and added costs to those imports are felt far beyond its ports. If import prices continue to rise, overall inflation would likely follow, pushing already high prices even further for American consumers.

Story editing by Shannon Luders-Manuel. Copy editing by Kristen Wegrzyn.

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

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The states where people pay the most in car insurance premiums

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Cheap Insurance compiled a ranking of the states where people pay the most in full-coverage car insurance premiums using MarketWatch data.
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Nearly every state requires drivers to carry car insurance, but the laws vary, and many factors affect the cost of coverage.

Some are controllable, at least to degrees: the type of car you have and your credit history. Some are not: your age and gender. Your marital status, place of residence, and claims history are among the other variables that go into it.

Across the United States, premiums are soaring, rising 20% year over year and increasing six times faster than consumer prices overall as of December 2023, CBS reported. Last September, CNN noted that car insurance rates jumped more in the previous year than they had since 1976.

CBS pointed to many potential reasons for these increases in prices. Coronavirus pandemic-era issues have made buying, fixing, and replacing vehicles costlier. Extreme weather events caused by climate change also damage more vehicles, while insurance companies are increasing their business costs. Severe and more frequent crashes are to blame as well, CNN reported.

On top of these, local factors such as population density, the number of uninsured drivers, and the frequency of insurance claims all affect premiums, which can lead motorists to change or switch their coverage, use other modes of transportation, or even alter decisions about when to buy a vehicle or what to look for.

To see how geography affects cost, Cheap Insurance mapped the states where people pay the most in car insurance premiums using MarketWatch data. Premium estimates were based on full-coverage car insurance for a 35-year-old driver with good credit and a clean driving record. Data accurate as of February 2024.


A heat map showing full-coverage car insurance premiums across the US

Cheap Insurance

Americans pay $167 per month on average for full-coverage insurance

There are common denominators among the five states where it’s most expensive to have car insurance: Michigan, Florida, Louisiana, Nevada, and Kentucky. Washington D.C. is another pricey locale, ranking #4 overall.

Three of these six are no-fault jurisdictions and require additional coverage beyond coverage to pay for medical costs. Michigan notably calls for $250,000 in personal injury protection (though people with Medicaid and Medicare may qualify for lower limits), $1 million in personal property insurance for damage done by your car in Michigan, and residual bodily injury and property damage liability that starts at $250,000 for a person harmed in an accident.

Other commonalities between these states include high urban population densities. At least 9 in 10 people in Nevada, Florida, and Washington D.C. live in cities and urban areas, which leads to more crashes and thefts and high rates of uninsured drivers and lawsuits. Additionally, Louisiana, Florida, and Kentucky rank #5, #8, and #10, respectively, in motor vehicle crash deaths per 100 million vehicle miles traveled in 2021 based on Department of Transportation data analyzed by the Insurance Institute for Highway Safety.

A highway in Louisville.

Canva

#5. Kentucky

– Monthly full-coverage insurance: $210
– Monthly liability insurance: $57

A car driving through the desert and mountain scenery in Nevada.

Canva

#4. Nevada

– Monthly full-coverage insurance: $232
– Monthly liability insurance: $107

Cars parked on a street in New Orleans.

Canva

#3. Louisiana

– Monthly full-coverage insurance: $253
– Monthly liability insurance: $77

A bridge over turquoise water.

Canva

#2. Florida

– Monthly full-coverage insurance: $270
– Monthly liability insurance: $115

A truck on a highway surrounded by Fall foliage.

Canva

#1. Michigan

– Monthly full-coverage insurance: $304
– Monthly liability insurance: $113

Story editing by Carren Jao. Copy editing by Paris Close. Photo selection by Lacy Kerrick.

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

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How businesses can protect themselves from the rising threat of deepfakes

Dive into the world of deepfakes and explore the risks, strategies and insights to fortify your organization’s defences

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In Billy Joel’s latest video for the just-released song Turn the Lights Back On, it features him in several deepfakes, singing the tune as himself, but decades younger. The technology has advanced to the extent that it’s difficult to distinguish between that of a fake 30-year-old Joel, and the real 75-year-old today.

This is where tech is being used for good. But when it’s used with bad intent, it can spell disaster. In mid-February, a report showed a clerk at a Hong Kong multinational who was hoodwinked by a deepfake impersonating senior executives in a video, resulting in a $35 million theft.

Deepfake technology, a form of artificial intelligence (AI), is capable of creating highly realistic fake videos, images, or audio recordings. In just a few years, these digital manipulations have become so sophisticated that they can convincingly depict people saying or doing things that they never actually did. In little time, the tech will become readily available to the layperson, who’ll require few programming skills.

Legislators are taking note

In the US, the Federal Trade Commission proposed a ban on those who impersonate others using deepfakes — the greatest concern being how it can be used to fool consumers. The Feb. 16 ban further noted that an increasing number of complaints have been filed from “impersonation-based fraud.”

A Financial Post article outlined that Ontario’s information and privacy commissioner, Patricia Kosseim, says she feels “a sense of urgency” to act on artificial intelligence as the technology improves. “Malicious actors have found ways to synthetically mimic executive’s voices down to their exact tone and accent, duping employees into thinking their boss is asking them to transfer funds to a perpetrator’s account,” the report said. Ontario’s Trustworthy Artificial Intelligence Framework, for which she consults, aims to set guides on the public sector use of AI.

In a recent Microsoft blog, the company stated their plan is to work with the tech industry and government to foster a safer digital ecosystem and tackle the challenges posed by AI abuse collectively. The company also said it’s already taking preventative steps, such as “ongoing red team analysis, preemptive classifiers, the blocking of abusive prompts, automated testing, and rapid bans of users who abuse the system” as well as using watermarks and metadata.

That prevention will also include enhancing public understanding of the risks associated with deepfakes and how to distinguish between legitimate and manipulated content.

Cybercriminals are also using deepfakes to apply for remote jobs. The scam starts by posting fake job listings to collect information from the candidates, then uses deepfake video technology during remote interviews to steal data or unleash ransomware. More than 16,000 people reported that they were victims of this scam to the FBI in 2020. In the US, this kind of fraud has resulted in a loss of more than $3 billion USD. Where possible, they recommend job interviews should be in person to avoid these threats.

Catching fakes in the workplace

There are detector programs, but they’re not flawless. 

When engineers at the Canadian company Dessa first tested a deepfake detector that was built using Google’s synthetic videos, they found it failed more than 40% of the time. The Seattle Times noted that the problem in question was eventually fixed, and it comes down to the fact that “a detector is only as good as the data used to train it.” But, because the tech is advancing so rapidly, detection will require constant reinvention.

There are other detection services, often tracing blood flow in the face, or errant eye movements, but these might lose steam once the hackers figure out what sends up red flags.

“As deepfake technology becomes more widespread and accessible, it will become increasingly difficult to trust the authenticity of digital content,” noted Javed Khan, owner of Ontario-based marketing firm EMpression. He said a focus of the business is to monitor upcoming trends in tech and share the ideas in a simple way to entrepreneurs and small business owners.

To preempt deepfake problems in the workplace, he recommended regular training sessions for employees. A good starting point, he said, would be to test them on MIT’s eight ways the layperson can try to discern a deepfake on their own, ranging from unusual blinking, smooth skin, and lighting.

Businesses should proactively communicate through newsletters, social media posts, industry forums, and workshops, about the risks associated with deepfake manipulation, he told DX Journal, to “stay updated on emerging threats and best practices.”

To keep ahead of any possible attacks, he said companies should establish protocols for “responding swiftly” to potential deepfake attacks, including issuing public statements or corrective actions.

How can a deepfake attack impact business?

The potential to malign a company’s reputation with a single deepfake should not be underestimated.

“Deepfakes could be racist. It could be sexist. It doesn’t matter — by the time it gets known that it’s fake, the damage could be already done. And this is the problem,” said Alan Smithson, co-founder of Mississauga-based MetaVRse and investor at Your Director AI.

“Building a brand is hard, and then it can be destroyed in a second,” Smithson told DX Journal. “The technology is getting so good, so cheap, so fast, that the power of this is in everybody’s hands now.”

One of the possible solutions is for businesses to have a code word when communicating over video as a way to determine who’s real and who’s not. But Smithson cautioned that the word shouldn’t be shared around cell phones or computers because “we don’t know what devices are listening to us.”

He said governments and companies will need to employ blockchain or watermarks to identify fraudulent messages. “Otherwise, this is gonna get crazy,” he added, noting that Sora — the new AI text to video program — is “mind-blowingly good” and in another two years could be “indistinguishable from anything we create as humans.”

“Maybe the governments will step in and punish them harshly enough that it will just be so unreasonable to use these technologies for bad,” he continued. And yet, he lamented that many foreign actors in enemy countries would not be deterred by one country’s law. It’s one downside he said will always be a sticking point.

It would appear that for now, two defence mechanisms are the saving grace to the growing threat posed by deepfakes: legal and regulatory responses, and continuous vigilance and adaptation to mitigate risks. The question remains, however, whether safety will keep up with the speed of innovation.

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