PALO ALTO, Calif.--Bill Clerico may not be Steve Jobs, but he's doing something very Jobsian: "I'm pushing people to do things they don't think are possible."
Clerico is CEO of, an online payments collection service that is taking on the likes of PayPal, Stripe, Braintree, and others, and which is growing--fast. Its 2012 revenues will likely be several times that of 2011, and that means a big expansion in users and employees. Plus long hours and hard work for those already on staff.
It's nearly 10 a.m. on a recent Monday, and I've dropped in to shadow Clerico for my Day on the Job series. He would have been in at 8:30, but he's just arrived after working until 2 a.m. last night on WePay's 2012 financial plan. He needed a little more sleep.
In just a few days, Clerico will be presenting the plan to the company's board, so he'd stayed up late Sunday night crafting a complex framework for the company's growth. But fueled by a huge Starbucks iced coffee, he's charged up for Monday. And as the late Apple CEO would have, Clerico expects nothing less of his team. "I'm going to [have to] push people to do more than what's reasonable," Clerico said. "And they're going to push back."
Meeting in a cage
It was time for WePay's weekly 10 a.m. Monday staff meeting, so everyone filed up some stairs into a cage-like room framed by chain-link fencing in the back of the company's offices.
At the meeting, each department head gave an update on what happened last week. Clerico kicked it off. "Good week last week," he said. "We set an all-time record" for fees, up substantially from the week before. Everyone cheered.
The meeting was also the latest opportunity to introduce several new hires. And no wonder: WePay's headcount surged 20 percent in October alone.
As each person presented, Clerico moved. First he sat alone up front, and then he stood against a whiteboard. Next he took a seat in the second row, and finally he sank into a bean bag.
Recently, WePay had gotten a big usage bump by becoming the fundraising service of choice for Occupy Wall Street. Director of community Sophie Monroe explained that WePay's customer support team set a record for calls the previous Monday. Someone wondered if that was due to Occupy Wall Street.
"No," Monroe said. "Occupiers don't call."
Clerico laughed. "They use those voice changers," he said.
Pumpkins and utensils
If you didn't know that Clerico is WePay's CEO, you wouldn't pick him out as its leader. He's 26, but he looks younger. Today he's wearing Nikes, jeans, and an untucked dress shirt over a white T-shirt. His desk is crammed unceremoniously between two others. Yet he's doing well enough that he recently appeared on an episode of Bravo's reality show "Millionaire Matchmaker."
WePay's offices, however, remain a bit on the dorm-like side. Fifteen rotting jack-o-lanterns greet anyone coming in the front door, and the kitchen sink was stuffed with dirty utensils from the previous Friday.
But this is inconsequential window dressing to a company that's raised $9 million in two rounds of venture funding, and which is now attracting a number of unsolicited financing calls.
As CEO, Clerico's schedule would usually be packed with candidate interviews, but this week, he's mainly focused on the board meeting. "Generally, the week before a board meeting," he said, "I've got to do real work."
One of the biggest questions the four-person board will be pondering is whether WePay should be financially aggressive or conservative in 2012. Should it raise more money? Explode the headcount?
"We raised a big round last year, and we have lots of cash in the bank," Clerico said. "We're growing like crazy, but is there an opportunity to grow even faster? If we don't grow, we die."
Conservative or 'balls to the wall?'
For a company like WePay, growth is a function of technology. So for an hour, Clerico has a product and engineering meeting with co-founder and COO Rich Aberman, CFO Chris Min, and VP of engineering Aleksey Sanin. On the whiteboard, Clerico had written "Do not erase" late last night on top of "2011/2012 Product Roadmap."
Starting off, the four negotiated Sanin's various staffing needs. As they debated, Clerico and Sanin would step to the whiteboard and write in a "+1" or "+2" in rows marked "Back end," "Front end," or "QA," and in columns corresponding to WePay's coming fiscal quarters.
The baseline is the conservative plan, done with a blue marker. The "let's go crazy, go balls to the wall" plan is in green. Sanin needs people for mobile app development, a support forum, system administration, quality assurance, and more. Some jobs require senior people, while others can go to cheaper junior hires. There was a bit of horse trading as Sanin asked for one type or other of employee, and Clerico would move a "+1" from one slot to another.
Finally, there was a blue 2012 roadmap adding 13 engineering hires to the current six. Green added seven more. Clerico grabbed his iPhone and snapped a few pictures of the plan. "So you can't change your mind later," he teased.
Unsurprisingly, the question of choosing the blue or green plan will come down to cost. "That's a decision that I and the board have to make," he explained. "My guess is we're going to go big."
A little while later, Clerico ushered Monroe, the company's head of community, into the conference room to discuss 2012 plans for WePay's operations department. At 21, Monroe may be one of the youngest such company officials in the Valley. She quit Boston College a couple years ago after interning at WePay and, Clerico said, basically holding the company together.
Now she has to help determine the resources WePay will put into support.
While PayPal is the undisputed leader in the payments field, its customer service reputation is horrible. One way WePay differentiates itself is with quick responses to users. That means offering 24/7 help by email, phone, and chat.
Over the next hour, Clerico, Monroe, and Min tried to figure out exactly what it costs WePay to support a user. One conclusion: Its operations team of three handles an incredible volume, easily more than hundreds of interactions each per day. Monroe argued WePay can't scale its support operations without adding staff and dividing duties. "We can't do [more] until we have at least two people just doing calls," she said.
As they talked, Min tried to calculate how much WePay customers are worth to the company, and how much support transactions costs. The company may well be in the red on operations, he concluded, but Clerico didn't care. "I'm okay being underwater on customer service," he said.
Monroe's team has another essential task: ensuring that payments aren't fraudulent. This is done via both automated and manual risk analysis systems and the company is always working on developing new systems that are intended to accelerate the process. But operations is still currently responsible for handling thousands of weekly reviews.
"Oh, Jesus Christ, that's a lot," Clerico said. "How is that possible?"
"I look at an awful lot of payments per day," Monroe responded.
For the most part, reviews are quick, involving little more than confirming that both parties are legitimate. But some require extensive research. So WePay has to figure out how many new people it needs to handle its expected explosion in volume.
Clerico was ready to throw bodies at the problem. "Sweet, let's go hire someone," he said. "We might have to overpay for the first person, but as we scale, the next guy will be cheaper, because we'll have more process in place."
Going over the deck
Though it was already almost 6 p.m., Clerico's day was hardly over. He wanted honest help with his board presentation, so he'd invited over Dan Rosen, a principal at WePay's lead second-round investor Highland Capital.
Rosen had already looked at the presentation, and he arrived loaded for bear with constructive criticism. "I'm going to give it to you straight," Rosen began.
"Be rough," Clerico said. "I hate it when people tell me I'm doing a good f------g job."
At that moment, the presentation featured a WePay product overview, a demo video, a breakdown of its customers, some graphs showing revenue and user growth, a comparison of the cost and value of the average account, and more.
Rosen quickly went through the slides, pointing out several he thought "sucked" and some he liked. He said that most of the content Clerico needed was there, but some wasn't.
For more than an hour, the two pored over the slides, rewriting some and deleting others. They spent at least half an hour trying to pinpoint WePay's competition. "You want to blow people away right away," Rosen said. "People are checking out at the end."
The board meeting
Given that so much of my day with Clerico was about his preparations for the board meeting and the question of whether WePay would go all in next year, I asked him later about the outcome.
"The board was excited how about much [we've grown]," Clerico told me by email. "We're going to be aggressive next year. We have a product our customers love and we're growing fast. [There's] no reason to ease off the gas."
If your company is interested in being featured in Day on the Job, please send a note to daniel-dot-terdiman-at-cbs-dot-com. Unless given specific permission, I will not reveal any proprietary information or forward-looking business plans I encounter during my time at the companies I visit.
Update, 1:40 p.m. PST: This story has been partly rewritten to reflect a more accurate number of WePay's daily customer service interactions and the extent to which the company's risk analysis systems are automated.