BTM Q&A: Manager of Sales & Sales Operations at Digital Ocean : Kevin Chiu

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For today’s Q & A, we’re publishing our chat with Kevin Chiu, the sales and sales operations manager at DigitalOcean.  Prior to that he helped build the SDR team for a applicant tracking startup called Greenhouse.

Best piece of advice you’ve received from a mentor:

The best piece of advice I’d ever received from a mentor was at my first job out of college. I was about 4 months into the job and they had opened up an internal team lead position. Needless to say, I definitely applied for it and wanted it bad. Although I was the top performer on the entire team, the interview process was still incredibly gruesome. I remember it until this day as if it happened last week. For the final interview question, my VP of Sales asked me who was the hardest working person on the team. As a 20-something year old, I had never been asked this before and I thought it was a trick question. I thought to myself, if I say I’m the hardest working on the person, that might come off as arrogant so I said another teammate (let’s call her Marissa) was the hardest worker (she really was at the time and I still believe it to this day). After I left that room, that answer ate me up. I couldn’t sleep that night and thought about what I could’ve said differently. The next day I walked up to my VP of Sales and told him I had a better answer… I told him that what I meant to say was that “Marissa” worked harder but only for herself. I worked a lot harder for the team and that’s why I deserved the Team Lead position. I said, I work smarter and not harder. He smiled at me as if he really appreciated that answer.

About an hour later, he walked upstairs to the sales loft (not the actual Salesloft but literally… it was a loft near the rooftop with 12+ young and hungry inside sales reps. My VP got everyone’s attention in the room and said “raise your hand if you believe in working smarter not harder.” About the entire room raised their hand — including myself. He then looked at us all and said I think you’re all fools. The people who win in this world are the ones who work smarter AND harder. Not the ones taking shortcuts. Hard work will out perform smarts any day. The room was silent and he walked away shortly after.

I’ll never forget that day and needless to say, I’ve had a work smarter AND harder mentality to this day.

How do you get buy-in from people you are managing:

There are two sides to this:

1) If you’re getting promoted from within, you have to have been a top performer. If not 1st, at least 2nd best but on the contingency that the #1 sales rep is a better individual contributor than he/she is being a manager and everyone knows it. You can’t have the respect of your sales team if they can’t trust that you’ve done it before so they can go to you for help when they need it.

2) If you’re getting brought in as a manager from the outside, roll up those sleeves and get your hands dirty. Show them that you have what it takes to do what they do every single day and that you have done it before. Nobody buys in to the person barking orders who hasn’t showed them that he/she’s got the grit or tenacity to do what they do.

How important is your sale stack technology:

Very, very important. I’m a huge believer in sales technology and am always 2-steps ahead with what’s out there in the market. There are always going to be the old school guys that can make sales by picking up the phone and using a phone book but 9 times out of 10, if you get that same exact rep but give them the right tools to automate tedious aspects of sales: prospecting, data entry, cleaning contact info, etc – they’ll invest twice as much energy into revenue-generating activity and generate twice as much revenue for your company.

Most important thing to learn for new sales managers:

Sales reps need to be approached similar to prospects. Instead of calling it a buyer persona, I think of it as “rep persona”. Not all sales people are created equally and are going to be different in some shape or form. One person is going to be better at calling and the other will be better at cold emailing. One might be able to take harsh feedback and needs that to be motivated but the other only needs a little bit of positive reinforcement to get the best out of them. With that being said, what works in terms of feedback and motivation for one rep, is not going to work for the other. Understand your team dynamic, how each rep works, what are each of their strengths and weaknesses, and what motivates them. Once you’ve figured all of that out, you’ll know how to get the best out of each and every single individual.

What do you think of cold calling? Should sales teams be using it?

I think there are certain businesses that need cold calling to connect with their buyers. You have to understand what your ideal customer profile looks like and what the best channel is to reach out to them in. For example, if you take a look at companies that are very transactional reaching out the SMB market (Yelp targeting mom and pop shops), you’re not going to get these small business owners via email or LinkedIn. The best channel is to call them directly on the phone at the store. For DigitalOcean, we’re targeting CTOs or VPs of Engineers at fast growing startups. If you take a look at the CTO at a company that’s around 100-200 employees, he likely isn’t going to have a landline sitting at his desk to be cold called on. With that being said, figure out what channel is going to give you the highest probably of connecting with your potential buyer. If that happens to be the phone, don’t just call at random. Be smart about when and how you call. Utilize seek lists for time zones, have research done prior, and use sales tools that help you track your prospect’s engagement with your collateral or let you know when they open an email so you can follow up efficiently.


FullSizeRender (1)Kevin Chiu is currently the Manager of Sales and Operations at DigitalOcean, a simple and fast cloud hosting service that provides an infrastructure experience that developers and startups love.

Prior to transitioning to the cloud infrastructure market, Kevin joined Greenhouse Software as the 50th employee and 10th sales hire to help scale the sales development team at Greenhouse Software to over 20+ inbound and outbound SDRs.

Before moving to NYC to focus on top-of-the-funnel lead gen, Kevin led the first full cycle inside sales team over at FiveStars in San Francisco, a YCombinator startup & #1 leading B2B loyalty SaaS platform that built a loyalty network and was focused on helping small to medium sized businesses increasing their customer spend and retention.

During his free time, he enjoys all things sales-related and hosts a monthly SDR meetup with NYC/SDR in addition to training an outbound sales workshop at SalesHacker, Inc and hosting their New York Series Events.