The Sales Influencer Series Presents: Drew Woodcock

Welcome to Episode 23 of the Sales Influencer Series, a podcast featuring the brightest minds in B2B sales and marketing. In today's episode, Ambition's Jeremy Boudinet welcomes ChowNow VP of Sales Drew Woodcock, who has taken ChowNow from 7 to 40+ sales reps in under 3 years. Hear Drew's story below.

Ep 23. How Sales VP Drew Woodcock Scaled ChowNow

Interview Topics

Introductions 0:00 - 4:57.

ChowNow works with restaurants all across the country, giving them a platform, mobile apps and Facebook app that lets restaurants take and deliver orders online. ChowNow also provides clients with a back-end CRM that helps them understand their customers and use that data through marketing. The company also partners with couriers to provide delivery opportunities to restaurants.

Drew fell into sales upon graduating from college. He had also had an interest in technology and communications. He worked for a number of small to medium-sized businesses over the first few years of his career. At LivingSocial, he was introduced to the founders of ChowNow. When he met them, he saw that they had the vision to do something great. ChowNow set out to have great local brands accept local orders via their own platform, rather than paying a percentage to a middleman, and give them something they can own and control.

Drew joined ChowNow in May 2013 and became sales manager within 7 months. Over the next 3 years, the team under Drew has scaled to over 40 reps.

Drew's Beginnings at Chownow. 4:50 - 8:10.

Drew joined ChowNow in May 2013 and became sales manager within 7 months. Over the next 3 years, the team under Drew has scaled to over 40 reps.

When Drew got to ChowNow, there were just under 30 people at the entire organization, only 5 of which were in sales. And as many people in technology sales can relate to - even though the technology was amazing and there was product-marketing fit, selling the product was a little harder than initially expected.

There was no sales manager at the time Drew was hired. He and his fellow reps got together every day, put their heads together and tried to figure out how to sell ChowNow. Some worked remotely. All reported directly to the Co-Founders. Because there was no one in management to dedicate themselves to laying out the playbook to the team, they all struggled.

Drew saw that the fellow members of his team were both very passionate about the product and very talented sales professionals in their own right. Though he was the newest hire on the sales team and beneath several higher performers, he went to the Co-Founders with a plan, modeling out the idea to scale the team and sell the product.

So Drew put together the outline of a playbook. And though the Co-Founders were initially hesitant, they eventually agreed to give Drew the lead. He started at the top - outlining the buyer personas, explaining why they would buy from ChowNow, how ChowNow would make their life better, why they would choose ChowNow and what things will look like 6-12 months down the road if they buy ChowNow.

How Drew Started Scaling Chownow. 8:10 - 13:00.

Drew's playbook achieved meaningful growth very rapidly. And though his numbers were great, he emphasizes that the human aspect of sales were what drove his success.

Drew's success began by rewriting the compensation plan that would drive his team by paying them more if they worked a little bit harder. They put it into place, showed each rep what they thought they could make if they hit their numbers and explained the "why" behind the plan to each rep.

Drew also showed the results they thought were possible and the activity that led to success - based on what they could measure previously. Salesforce was out of the box when Drew got there, so he stayed up late teaching himself the platform. As sales manager, his goal was to ensure that Salesforce aligned with the prospect throughout the buyer's journey.

Once the compensation plan was set up, it started working and the reps started buying into it. From there, Drew was able to start diving into the methodology, sales skills and buying stages each prospect would go through to in order to qualify as a lead in their buyer's journey.

They spent a long time on that and started using the data in Salesforce to assess what made a great account a great account. They then created a tier system to have reps better qualify restaurants based on Yelp! reviews, take-out and delivery volume and some other data points. By having the reps focus on the restaurants they knew were most likely to succeed, ChowNow was able to make their reps much more efficient and spend more time having conversations with the right restaurants.

ChowNow aligned with a great company called Sidewalk. They went to them and said, build us a list of companies with these attributes, and they gave ChowNow thousands of leads, which they assigned out to their reps. Once they saw the win-rates go up, ChowNow kept doing that. As they've scaled, they had to rearranged the format - but that is where it started.

How Drew Scaled & Segmented His Team. 13:00 - 17:16.

When the team was small, there were a few remote people. As the team grew, it became important to specialize the roles and create focus. When reps lack focus, it's hard to stay organized.

Drew made the remote people outside reps and the local people inside reps. He hired several one-off reps as well. From there, Drew saw his outside reps struggling - they would have a great month, then a bad month. And the problem was, there wasn't enough time in the day for them to meet with restaurants and set up new opportunities for themselves, due to the weird hours of restaurant owners.

So Drew tested out SDR roles for the outside reps, and it worked extremely well and led to more consistent production. The next group of hires Drew made was a group of 9 people in each role: 3 Inside Reps, 3 Outside Reps and 3 SDRs. They learned a lot during this period. Drew did a lot of self-analysis on what he was hiring for and whether they were the correct things to be hiring for based on how the reps developed and performed.

ChowNow spent all of 2015 continuing to hire, focusing more on the outside team because they tended to be more consistent and efficient, and clients wanted to close deals with someone they could look in the eye and know that they had someone local to come deal with issues should anything go wrong. The inside team scaled to 7 and the outside team went from 5 to 22 over the course of 2015.

At the end of the day, success is all about making good hiring decisions and having an effective training program. ChowNow has a very detailed training program that tests competency of product, deploys role-playing situations, sends new hires into the field with local reps to see how selling ChowNow works, and has them shadow every sales-oriented team and meeting other departments to see what life is like after the sale.

The commitment ChowNow has given to its training program plays a huge part in the success of reps. ChowNow has just 1 outside sales manager for 18 people, all of whom are executing at an extremely high level. ChowNow's training program - plus the fact that the reps are great salespeople - are what has enabled ChowNow to succeed.

ChowNow's Sales Training Program: 17:16 - 20:19.

Synopsis: For freshly-minted hires, ChowNow has a full week of classroom-style training at headquarters to review company history, culture and product, meet department heads, do shadowing and so forth.

The 2nd week, the company sends an experienced team member out in the field with new hires to attend initial sales meetings. ChowNow makes sure that each new hire has a full slate of meetings their first week, plus a manager alongside them to answer questions, help them run meetings and make sure they do all the right things in their CRM.

After the first 2 weeks, ChowNow provides ongoing training via an LMS that has courses on partnerships, deeper dives into the product and the like. Drew's team has learned that it's important to give reps the tools they need to succeed in those first 2 weeks, then provide further training every few weeks with courses they can take on their own time, Q&A sessions done via Skype call, and so forth.

How Drew Aligns Sales & Client Success. 20:19 - 25:42.

Drew has learned over the years how important it is to set expectations and align teams in order to reduce churn. His sales team works very closely with ChowNow's restaurant success team to ensure client satisfaction.

In Mark Kosoglow's interview, he talked about using a pod structure to scale his SaaS sales team. ChowNow tried that early on, but has been unable to stick to that because it can't predict the volume of any one rep. With that said, Drew believes in the pod concept and would love to implement it in the very near future. In the interim, Drew has instead built a very heavy instance in Salesforce to manage workflow on the part of the customer success team.

That's key - because a huge part of what ChowNow offers is excellent customer support. The restaurant success team works closely with sales to ensure that restaurants know exactly what ChowNow needs from them once they come onboard so ChowNow can build their platform with as little work as possible on their end.

To that effect, ChowNow puts a lot of work into handoffs. Something ChowNow has found to be successful his a simple email handoff from sales to customer support introducing the client success person. That small practice has done wonders in cutting onboarding time, making the prospect comfortable and expediting the launch of their product.

ChowNow also does a 30-60-90 day check-in program with each client to make sure customers are okay with the product and don't need any help. Something else Drew just implemented is a new type of customer success role who calls client restaurants past the 90 day mark, reviews the trends with customer behavior and helps them understand how to optimize their experience.

To Drew, the entire customer journey is very important - from initial interest to the duration of their lifetime as a client. As Head of Sales, Drew wants to ensure ChowNow is capturing as much value at as many different points as he can - which is the best way is to ensure that each customer has a great experience all the way through. In talking to current clients, Drew has better understood typical customer objections and used those conversations to better equip his reps to face them.

How Drew Builds Great Sales Culture. 25:42 - 30:15.

Synopsis: It's not often in sales that reps are really passionate about what they're selling, or feel like they're making a difference in the communities they serve. At ChowNow, reps know that they're selling a product that can help restaurants survive. Restaurant owners have the odds stacked against them - 70 percent of restaurants don't even make it a few years.

ChowNow believes deep down that they have a great product that can help these businesses create more quantifiable revenue and better serve their customers, who ChowNow reps also happen to be in the cycle of things, as food consumers. Drew's team has a mantra: "Defend the shield." The shield is the ChowNow logo.

Everyone believes in the mantra, which has helped ChowNow has created a culture of people who love food, love restaurants and truly believe they can help them succeed. ChowNow reps always go after the greatest, coolest and sexiest local restaurants with the mission to get in their corner and help them succeed.

The spirit of "Defend the shield" is what Drew's team believes in. ChowNow has great perks - ping pong table, snacks, et cetera - but that's not culture. Culture is a team of people who want to beat each other because they're competitive, but moreso want to win together as a team. And each week, Drew's team reviews the tape and sees where they succeeded, where they made mistakes and where they can get better.

ChowNow reps truly want to develop their skills and master their craft. They've had some great people part ways, not because they were poor performers or dissatisfied with ChowNow, but because they had excellent new opportunities come before them. And as a leader, that's what Drew wants: To have his reps leave ChowNow way better than when they got there. It's a culture of people who want to succeed. They want to make money, of course. But they also want to win and be the best at what they do.

Drew's goal is for his team to be excited about who they're working with. He wants to be as transparent as possible, include the team on decision-making, have them understand why changes are effectuated and get feedback from them on all major decisions facing the company and sales team, in particular. He's learned it's much better to have everyone onboard with a new process before launching it, as opposed to coming to them and saying, "here's the new process."

How Drew Uses Ambition. 30:15 - 33:10.

Synopsis: Drew has been using Ambition since the fall of 2014. He appreciates Ambition for sticking with him, listening to his feedback and quickly evolving the product to meet his needs. ChowNow uses Ambition in its sales team and restaurant success team. Drew thinks the restaurant success team members got excited when they saw the sales team enjoying Ambition features like User Anthems, TVs and Triggers when they closed deals or achieved success and they wanted in.

Drew has always told the team that each team member knows his or her numbers - and if those numbers are hit, you can go home feeling good about what you're doing. Even if you didn't close a deal that day, if you created opportunities or hit the activity level you need to, you can trust by the end of the month that you'll be where you need to be. And if you fall below activity level, you need to be sure to make up for it the next day.

Ambition gives ChowNow an awesome opportunity to put all that information front and center. They have two 80 inch screens right in the center of the office - and it creates a healthy, competitive environment that tells everyone where they stand. Drew appreciates what Ambition has done to encourage rep activity and keep it fun and exciting.

Signing Off. 33:10 - 34:50.

Synopsis: Drew thinks sales is the coolest job in the world. He doesn't know who is having more fun than the best salespeople. In today's world, the opportunity to be a true sales consultant is better than ever. The information available to sales professionals and cool tools coming out make it a great place to be.

Any restaurant owners out there listening, go to ChowNow.com. Drew would love to chat with you and discuss what it would be like to work together. In general, LinkedIn is a great place to get in touch with Drew. He's also trying to get better on Twitter - his handle is drwoodcock. Drew is always looking to learn more about the sales operations and enablement side of things and use tools without sacrificing human touch.

The Sales Influencer Series Library

To check out further episodes and see why CloserIQ has ranked the Sales Influencer Series as one of the very best sales podcasts of 2016, just click on the links below.

Episode 1. John Barrows

Episode 2. Lori Richardson

Episode 3. Max Altschuler

Episode 4. Matt Heinz

Episode 5. Mark Leslie

Episode 6. Kyle Porter

Episode 7. Jon Bradford

Episode 8. Eks Anderson

Episode 9. Matt Hottle

Episode 10. Heather Morgan

Episode 11. Ilan Ferdman

Episode 12. Ryan Jenkins