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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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10 tips for managing payroll for small business owners

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Buddy Punch compiled a list of ways for small business owners to set up and maintain a bulletproof payroll system from a collection of expert sources.  
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It’s essential to closely manage company payroll in a way that best suits your specific business needs and supports your employees. Given the complexities of state and federal taxes and the importance of paying your staff on time, keeping good records sets you up for success as your business grows—whether you’re bootstrapping a startup or managing a team.

Buddy Punch leveraged a collection of expert sources to compile a list of ways small business owners can create and maintain a bulletproof payroll system. Central to these insights is the goal of building a secure and accessible payroll system that protects data and allows employees to access their personal information.

Small businesses may have to outsource specific parts of their payroll systems to experienced professionals to ensure compliance, while smaller companies can delegate these tasks to an individual. Keep reading to learn more about wise management of payroll systems, from picking the right software to staying in compliance.

A human resources worker using a payroll software.

Kaspars Grinvalds // Shutterstock

Select appropriate payroll software

Payroll software is far from one-size-fits-all, and there are several factors at play to keep in mind while shopping around.

From the ease of use and features to integrations and support, there are plenty of options to choose from. It’s wise to start by considering the number of employees at play before making a decision. Will you or your team be able to keep up with the demand for updating employee records? Remember that if you have remote employees, you’ll be responsible for their state and local taxes.

In addition to the number of employees, small business owners should consider what benefits are offered, when payroll will be executed, and who will administer it. Other factors—including the payroll budget itself—are worth keeping in mind to ensure the system you select will be right for your company.

A human resources employee looking at their calendar.

Rawpixel.com // Shutterstock

Create a payroll calendar

No matter which kind you use, calendars are part of our daily lives—and there’s no exception for a small business. A payroll calendar considers the pay periods and can track important IRS tax filings. Knowing what is due at a particular time allows payroll managers to plan and schedule payments to the government promptly and effectively.

Using a payroll calendar also helps a business manage available funds for payroll each pay period. If you decide to DIY your payroll calendar, consider using a template to organize employee pay and tax filings.

A payroll administrator making calculations.

Rostislav_Sedlacek // Shutterstock

Hire a payroll administrator

While some small businesses can get by managing their own payroll, there are times when outsourcing or hiring a payroll specialist or administrator may be necessary. A payroll administrator will keep the business up to date on tax regulations and employee changes and updates.

When hiring for this role, look for people knowledgeable about payroll laws, regulations, and taxes. Knowing when to hire a payroll administrator will depend on how many employees you have and if you support remote workers. Whether you decide to outsource or do it yourself, you’ll need someone to provide quality checks on your processes.

An office employee working on payroll.

Natee Meepian // Shutterstock

Keep payroll and operating expenses in separate accounts

The adage “Don’t put all your eggs in one basket” applies to managing payroll for your small business. Keep your bank account for payroll separate from your general operating expenses. Doing so will help your accountant track transactions and keep records updated.

See if your current bank can add another account for payroll with no added costs. While it may appear easier to keep all of the accounts connected, you’ll have more to manage as your business grows. Start out with a payroll clearing account to maintain financial security and allocation.

A deli worker calculating their taxes.

mavo // Shutterstock

Never dip into payroll tax funds

There are huge implications with the IRS for not paying payroll taxes. Although some businesses may need the money to take care of other business expenses, it’s never a good idea to borrow from your business’s tax funds. One option that small business owners may consider is taking out a loan to cover miscellaneous expenses rather than using payroll funds and risk missing important tax payments.

If your company uses payroll tax funds to pay for other operations, it may be time for a business audit. Consider creating a rainy day fund for your business to discourage any payroll account dipping.

A binder of payroll records.

docstockmedia // Shutterstock

Document your payroll process

Sweat the small stuff. No matter the size of your small business, keeping good records will serve your business well in the long run.

From one employee to multiple, it’s critical to keep meticulous records. The IRS expects you to maintain payroll records for at least three years. A well-documented process will help your business comply with tax laws and keep track of your employees’ pay and updates.

If you are the sole employee of your business, make it a habit to record everything: This process will allow you to see the overall health of your business and allow for future planning.

An old stack of payroll records.

RAGMA IMAGES // Shutterstock

Develop a thorough timekeeping system

Setting up a good digital system to track your employees’ time is crucial in making your business more efficient. Accurate timekeeping will help with accounting and payroll records—and there are plenty of resources that make the process easier.

Some low-cost options work with other business tools to streamline the process of payroll compliance. Consider outsourcing payroll timekeeping to meet the demands of your growing workforce.

An employee taking a survey about payroll.

Andrey_Popov // Shutterstock

Talk to employees about what works and what doesn’t

For young businesses, polling employee preferences can help settle certain payroll options. Some workers prefer biweekly pay periods, but others—often hourly employees—may prefer to be paid weekly. Take the opportunity to ask your employees what works for them and structure your system accordingly.

A business owner writing a check based on payroll data stored in their computer.

NIKCOA // Shutterstock

Keep employee info well-organized and secure

Protecting small-business payroll data is just as important as protecting data files, and secure systems will do both. Employees can access their payroll system to update records and view pay stubs, which should be made available through payroll system training. Ensure the integrity of your business by protecting your employees’ data. Implementing a strong payroll system includes limiting who has access to sensitive employee data.

President Joe Biden signing the Paycheck Protection Program Extension Act of 2021 into law.

JIM WATSON // Getty Images

Keep up with state, local, and federal payroll rules

Staying updated on payroll rules can keep your business running smoothly without the stress of audits or fines. Payroll systems will manage this for you.

For a business without the capacity or expertise to track local and federal changes, business owners should consider outsourcing this work to a contractor who can. Subscribing to local and federal mailing lists may be useful to stay abreast of new updates.

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

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Are the days of ‘Big Tech’ on their way out?

“These are cost-cutting measures, but if you talk to people in tech, they’re sort of emotional, cultural resets as well,” explains tech reporter Peter Kafka in podcast.

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Silicon Valley is having a bit of a rough go lately.

Layoffs at some of the biggest tech companies — 10,000 at Amazon and 11,000 at Meta for starters — have hit the sector hard, and there’s an air of downsizing all around. This means that in addition to letting staff go, even all those perks that many startups and long-established companies alike have used to lure top tech talent — think offices with stocked fridges, gyms, and shuttle services — have been reined in. 

A recent episode of Vox’s podcast Today, Explained dove into what’s happening in the tech world, speaking to Peter Kafka, a tech reporter at Recode

Here are three highlights from the conversation:

On the current landscape as an “existential shift”

I think most people who are working in tech have only been there during boom times. The last real deflation in tech was all the way back in 2000, 2001. There’s almost no one working in tech now who was around for that. So if you’ve been working in tech, you’ve only known things going up and to the right. You got paid a lot. There were always companies who wanted to hire you away from the company you were at, so you got paid even more. You knew that you could leave Facebook or Google and go to a startup, and if that startup didn’t work, maybe it would get bought by Facebook or Google.

And all of that comes to a record-scratch stop this year.

On the lack of growth in the sector

Yes. There’s a bigger story that goes back a couple of decades. These tech companies, Google, Facebook, Amazon, and Apple all had crazy, crazy, crazy growth. They were selling tons of ads. They were selling tons of iPhones. They reflected a big change in the way the world used technology. They were at the front of that. They got rewarded for that.

But those companies aren’t growing at the same rate anymore. Many of them are pretty old now — or their main product is pretty old. The iPhone is 15 years old. Google’s main search ad business is 20 years old. YouTube is 15 years old, more or less.

On the “fable and myth” of Silicon Valley

Yeah. I don’t want to be pollyannaish about this because people are losing jobs. And people are going to have a harder time paying rent or mortgages or feeding their families. But it’s part real and part fable of Silicon Valley to have this creative destruction where old things get taken down. New, cool things get built in their place. It’s part of the fable and myth of Silicon Valley that has a great deal of truth to it as well. 

And so there’s lots of folks saying, “All right, we’re going to go make something new. By the way, we made a bunch of money in the last couple of years, the last 10 years. We can afford to not be working at a Big Tech company for a while. Let’s go cast around for a new idea.”

Read the interview transcript or listen to the episode

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Jobs where you’re most likely to be single at 40

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Can an occupation influence your marital status? Stacker analyzed Census Bureau data to find jobs where you're most likely to be single at 40.
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Ever felt like your job was holding you back from meeting that special someone? You may be right.

To determine jobs where you’re most likely to be single at 40, Stacker analyzed data from the 2021 American Community Survey, powered by the Census Bureau. The percentage of never-married respondents was calculated by dividing the number of respondents who had never been married by the total respondents for a given occupation; this metric ranks the list.

Similarly, the percentage of single respondents was calculated by dividing the sum of the respondents who reported they were never married, widowed, divorced, or separated into the total respondents for a given occupation. Inevitably, there is overlap between those who said they were never married and those who are considered “single.”

Perhaps not surprisingly, many of these occupations are in the service industry, likely because employees in the service industry work long hours, evenings, and weekends and may not have time outside of work to find a partner. However, some blue-collar jobs also made the list.

The reality is that more people than ever are choosing to remain single longer, regardless of occupation. The Centers for Disease Control and Prevention found that the marriage rate fell from 8.2 marriages per 1,000 people in 2000 to 5.1 marriages per 1,000 people in 2020. People delay marriage for numerous, wide-ranging reasons, from feeling unprepared financially to not wanting to settle down.

Meanwhile, the number of unpartnered people continues to grow. The Pew Research Center found in 2019 that nearly 1 in 3 adults between 40-54 were unpartnered, compared to 1990 (almost 1 in 4).

Keep reading to discover the jobs where you’re most likely to be single at 40.

You may also like: 50 most physical jobs in America

Two cooks in commercial kitchen

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#30. Cooks

– Percent never married: 56.96%
– Percent single: 70.45%

Person carrying drinks to table

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#29. Food servers, nonrestaurant

– Percent never married: 57.27%
– Percent single: 70.38%

Bartender mixing drink

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#28. Bartenders

– Percent never married: 57.5%
– Percent single: 73.1%

Tour guide leading hike

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#27. Tour And travel guides

– Percent never married: 58.19%
– Percent single: 66.59%

Air transportation attendant

Olena Yakobchuk // Shutterstock

#26. Transportation service attendants

– Percent never married: 58.91%
– Percent single: 69.92%

You may also like: Jobs with the lowest divorce rates

Person washing vechile

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#25. Cleaners of vehicles and equipment

– Percent never married: 59.14%
– Percent single: 71.05%

Parking attendant in lot

Yevhen H // Shutterstock

#24. Parking attendants

– Percent never married: 59.37%
– Percent single: 70.06%

Person working in shipping room

Jacob Lund // Shutterstock

#23. Stockers and order fillers

– Percent never married: 60.3%
– Percent single: 71.93%

Two people holding dog in veterinary office

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#22. Veterinary assistants and laboratory animal caretakers

– Percent never married: 60.84%
– Percent single: 67.19%

Person buying movie tickets

Tyler Olson // Shutterstock

#21. Ushers, lobby attendants, and ticket takers

– Percent never married: 61.38%
– Percent single: 73.53%

You may also like: Former jobs of every Supreme Court justice

Telemarketer speaking with client

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#20. Telemarketers

– Percent never married: 61.45%
– Percent single: 74.78%

Construction worker carrying ladder

ephyr_p // Shutterstock

#19. Helpers, construction trades

– Percent never married: 62.48%
– Percent single: 70.51%

Person chopping vegetables

DenisProduction.com // Shutterstock

#18. Food preparation workers

– Percent never married: 62.52%
– Percent single: 75.17%

Soliders stand and salue

Bumble Dee // Shutterstock

#17. Military-enlisted tactical operations and air/weapons specialists and crew Members

– Percent never married: 62.8%
– Percent single: 67.08%

Person preparing hamburgers

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#16. Food preparation and serving-related workers, all other

– Percent never married: 63.76%
– Percent single: 70.03%

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Cashier working grocery checkout

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#15. Cashiers

– Percent never married: 65.88%
– Percent single: 78.08%

Recreation coach speaking with kids team

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#14. Recreation workers

– Percent never married: 66.2%
– Percent single: 75.92%

Woman cleaning tables

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#13. Dining room and cafeteria attendants and bartender helpers

– Percent never married: 66.83%
– Percent single: 77.07%

Man installing photovoltaic panels

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#12. Solar photovoltaic installers

– Percent never married: 67.%
– Percent single: 76.26%

Tutor assisting student

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#11. Tutors

– Percent never married: 67.04%
– Percent single: 72.93%

You may also like: Richest women in America

Person filling out job application form

Mangostar // Shutterstock

#10. Unemployed, with no work experience in at the last 5 years or more

– Percent never married: 68.88%
– Percent single: 79.78%

Note: This refers to those unemployed with no work experience in the last five years or earlier or those who never worked

Close up waitress taking order

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#9. Waiters And waitresses

– Percent never married: 69.95%
– Percent single: 79.64%

Dancers rehearsing at bar

Evgeniy Kalinovskiy // Shutterstock

#8. Dancers And choreographers

– Percent never married: 70.63%
– Percent single: 78.34%

Dishwasher cleaning in commercial kitchen

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#7. Dishwashers

– Percent never married: 70.95%
– Percent single: 81.66%

Man adjusting stage light

Oleksandr Nagaiets // Shutterstock

#6. Other entertainment attendants and related workers

– Percent never married: 71.16%
– Percent single: 79.38%

You may also like: 5 ways to take the stress out of traveling for work

Umpire on sports field

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#5. Umpires, referees, and other sports officials

– Percent never married: 71.62%
– Percent single: 77.28%

Students gathered in dorm kitchen

FXQuadro // Shutterstock

#4. Residential advisors

– Percent never married: 80.53%
– Percent single: 87.76%

Man working in food truck

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#3. Fast food and counter workers

– Percent never married: 82.68%
– Percent single: 87.63%

Baristas in coffee shop

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#2. Hosts And hostesses, restaurant, lounge, and coffee shop

– Percent never married: 83.88%
– Percent single: 89.06%

Prison attendant

Bigflick // Shutterstock

Protective service workers

– Percent never married: 90.1%
– Percent single: 92.13%

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