Modernizing Your Sales Organization for 2016 – Q&A with Skaled, Zenefits, Greenhouse

As we prepare to ring in the new year, we all begin to focus a little more intently on the future. What will 2016 bring? And what changes took place in 2015 that we need to be sure we’re adapting to going forward? We recently held a webinar on this very subjected titled, “6 Things Your Sales Organization Needs To Prepare for 2016,” where we sat down with top sales leaders from Zenefits, Grovo, Rocketrip, Skaled and Greenhouse.

Needless to say, the session was so jam-packed with great insights and lively conversation that the panelists ran out of time before they had a chance to do a Q&A. Fret not, they’ve taken the time to address most of the audience questions that came in here on the Sales Hacker blog! Huge thanks to Skaled for bringing together such a brilliant group of Directors and VPs. Enjoy and Happy New Year!

1. What are some ways you balance the focus of finding and signing up new logos and growing your footprint with existing customers?

jakeTypically these are two separate roles when possible, as the skills are different. If you have one person doing both, the simple rule is: your best customers are usually your current customers. This is NOT true though if the upsell potential is light. You have to know the market and upsell potential to know exactly what will impact revenue the fastest. – Jake Dunlap, CEO of Skaled


2. Question for Jake Dunlap: I work at a company in a similar market as Glassdoor’s. During your time as VP of Sales at Glassdoor, what was the ideal hiring profile that was developed for your account executives?

When we hired from the industry, it worked out less often than when we hired for people with SaaS experience. We switched our model and almost exclusively stopped hiring sales people from the space, but I know in later years, GD had success with a good amount of people from Careerbuilder as they teach a sales style similar to a SaaS model.

The other big piece we screened for was problem solving – people had to know how to position us in the space and understand the real value that we added to a business. We found from assessment testing that the people with poor problem solving skills were usually the ones that didn’t work out. – Jake Dunlap, CEO of Skaled


3. Do you require sales people and Sales Managers to show you their W2 forms from prior years?

I personally do not. However, I have been at companies in the past where it was required. For me, while past performance is certainly a factor, I’m not making my hiring decision based on it. My decision is based on what I have determined are the skills, traits & characteristics that will make someone successful in their role at this company. I am looking for candidates that can demonstrate those attributes. – Marc Jacobs, VP of Sales at


4. How often do you refine your qualification criteria? Is it automated?

Qualification criteria needs to be a constant and ongoing conversation between the marketing, SDR, and AE teams. Create a feedback loop between the teams and facilitate this constructive feedback. Push the envelope on how far you can take an initial discovery conversation with the goal of shaving time from the sales cycle. – Robby Allen, Director of Sales Development at Zenefits


5. How can we empower Millenials to create a self-learning Sales Organization that promotes leadership through knowledge sharing?

The company has to provide the environment for this to thrive. It’s a big fallacy that these things “just happen.” The company has to praise the top people and provide a platform for them to share their ideas. Then it makes it easier for this type of culture to take place. – Jake Dunlap, CEO of Skaled


6. What resources do you use to train cold callers?

Manager coaching, preferably every single day. Managers should spend a good deal of time side by side coaching when reps are cold calling. Use feedback forms to log in real time, and share feedback with the rep after each call blitz. Create accountability for feedback by uploading forms online and reviewing in 1×1’s. – Robby Allen, Director of Sales Development at Zenefits


7. What role does big data have in your plans to take your sales program to the next level in 2016?

This will be huge in 2016/17 with the rise of predictive analytics. We are already seeing dynamic lead scoring to make sure people are spending time with the right people based on historical analysis and behavior and we are now seeing lead routing using big data to get leads to the right people. The old way we assigned leads will be a thing of the past in the next 2-4 years as we use data to get the right leads to the right people and then get those people spending time with people who have the highest likelihood to buy. – Jake Dunlap, CEO of Skaled


8. What are some of your top resources to help you stay ahead of the trends? Favorite blogs? Books you’d recommend to the audience? 

I really enjoy First Round Capital’s blog as it puts out content on a variety of topics. I also recently read the book “Who” to tighten up the things we are doing in the interview process. We now recommend it to all of our clients. – Jake Dunlap, CEO of Skaled

Amy is a four-time founder (Nothin Network, acquired by AzoogleAds; EnableYourSpace, acquired by Copeac) and marketing consultant working in the B2B SaaS space. She is currently the Director of Marketing at Sales Hacker and a member of the marketing team at SaaStr, as well as the Co-Founder of Rock Bottom Publishing.

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