Interview with Jake Dunlap – The CEO at Skaled

The Sales Hacker team is interviewing our speaker lineup for the upcoming Sales Hacker Conference on April 30th in New York City. We’d like to give you perspective on who our speakers are and insights into their B2B startup experience, covering a variety of Sales topics such as Hiring, Building, Measuring, and Scaling sales.

Next up in our interview series we have Jake Dunlap, the CEO of Skaled. Jake worked as the VP of Sales at Glassdoor and as the Head of Product Outreach and Customer Success at Chartbeat. He started Skaled 3 years ago to help startups scale their sales organizations through tactical support. They’ve worked with over 40 different startups throughout the world and have he

What’s the Big Goal for Skaled this Year?

For most sales leaders, 2015 is in the bag. The things they’ve done over the last three months and the things they’ll do over the next two months will really dictate success over the next 6-12 months. What Skaled has done is invested in a couple areas. They’ve invested in some more senior level people and in systems and processes. As a company that is self-funded, it is important that they’re scaling as much and as smart as possible. They must continue to grow and refine their own internal processes to scale as efficiently as possible.

What’s Next for SDR Specialization?

Due to the tools and technologies that are coming out there will definitely be specialization in the role of the SDRs. Not so much for just an email or social SDR but for cadences (Day 1 is an email, day 3 is a social media touch, day 5 is a LinkedIn connect, etc). And what’s more, is instead of hiring SDRs who are straight out of school (the stereotypical SDR roles) we’re looking for more of project managers and content writers. A lot of what SDRs do is about the copy and can these people write good compelling content. It’s much different than the person who is overly gritty.

What is the High-Level Overview of Your Workshop at SHC NYC?

When it comes to outreach, it falls into three categories. Step 1 is who are we going to target. This is where a lot of companies struggle, because their target market always seems to be really broad. For example, “finance companies with 500-1000 employees” whereas in reality it is a sub-segment of a sub-segment. Honing in early on will save you lots of headaches and give you more traction than being broad. Step 2 is focused on the messaging to that specific buyer persona. And step 3 is all focused on the cadence.

What Era of Sales Are We In?

Sales Process Optimization because there’s no shortage of tracking in CRMs, but what I feel what is lacking is any ability to measure the effectiveness of sales processes and messaging. Sales Transparency is also beginning to take form. If you look at the B2C market you’ll see it is becoming more of a perfect market. Everything has a review site from housing, to jobs, to cars, to lawyers, etc. Software reviews site exist, but they’re not as genuine. Buyers are willing to give more information to ensure they’re getting the best deal, and sellers are becoming more consistent with pricing in exchange for more information from the buyers.

Craig is the Director of Marketing at Sales Hacker and the Founder of Red Bridge. A marketing agency focused on helping B2B Tech Startups accelerate their growth.

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