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Interview with Russ Heddleston, CEO, DocSend

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Russ Heddleston
[mnky_team name=”Russ Heddleston” position=” CEO, DocSend”][/mnky_team]
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“By aligning around the customer and his or her business goals, marketing and sales can finally overcome the organizational silos that often lead to disjointed messaging, wasted resources, and inefficiency in the pipeline.”

On Marketing Technology

MTS: Tell us about your role at DocSend and the idea behind starting a sales content management platform?
I’m the co-founder and CEO of DocSend. Before starting DocSend, i was a Product Manager for Pages at Facebook. One of the products I came across during my time there was an internal tool called Pixelcloud. It allowed you to do something that really stuck with me: Track who’s viewing your designs and photos.

In 2013, I teamed up with my co-founders, Dave and Tony, to apply that same idea to the content you share over email. But, first, we had to find a way around one giant barrier to tracking, the old-fashioned email attachment! Attachments are used so often, but they’re a real impediment to collecting information about a recipient’s level of engagement with content. This is what drove us to build DocSend, a powerful link-based system that allows you to see exactly when, where, and how people engage with the content you send.

Today, we enable sales and marketing teams at over 4,400+ companies, including Pinterest, Buzzfeed, and Upwork, to find and share the content that closes deals.

MTS: What are the tools and trends that are shaping the way B2B marketers communicate with their customers and partners?
One trend that really stands out to me is Account-Based Marketing (ABM), or the idea of treating every target account as a market of one. We practice it here at DocSend on both our sales and marketing teams. For us, ABM involves taking the time to map out stakeholders at target accounts, to really understand their pain points, and to sell into their organization by establishing a clear, actionable business case.

This is remarkably similar to how startup founders think about fundraising. In fact, tracking pitch decks was one of the first use cases for DocSend. As a founder raising money, like sellers and marketers reaching out to target accounts, you need to identify which investors are the best fit, figure out what they care about, and then do personalized outreach – all things enabled by unique, trackable links.

Another related trend is sales and marketing alignment. While it’s a problem as old as business itself, it’s finally getting the attention it deserves. I would argue that we need to add one more element to sales and marketing alignment: the customer. By aligning around the customer and his or her business goals, marketing and sales can finally overcome the organizational silos that often lead to disjointed messaging, wasted resources, and inefficiency in the pipeline.

MTS: Since DocSend’s inception, how has the documents analytics and intelligence market evolved with new-age customer experience expectations?
Over the last four years, I’ve found one thing to be true: We now live in a customer-centric world. A lot of it has to do with the rise of the internet. The internet has not only changed how we sell but also – and more importantly – changed how prospects buy. This is a really important distinction.

Today, buyers define their own journey, and it’s up to marketers and sellers to figure out how to win their attention and their wallets. One of the ways we can do that is by leveraging content throughout the sales process. And that’s made content analytics in the middle of the funnel, like the kind DocSend provides, more important than ever to high-performing organizations.

But the buyer’s journey doesn’t end once the purchase has been made. Customers expect, if not demand, products designed for them. From the very start, we’ve built DocSend to be the easiest product to use on the market, and we’ve heard that sentiment echoed by our customers. Reality is, customer experience now matters just as much as the robustness of your product.

MTS: How should CMOs better leverage documents analytic tools to refine their email marketing and sales enablement strategies?
The key to leveraging tools like DocSend is to establish clear benchmarks for success and the methods needed to track them. But, to back up slightly, the very first thing CMOs and other marketing leaders need do is get all their content into one place. Having a central library ensures that sellers can easily find and share approved content and that marketers can see what’s being used and by whom.

The next step is to identify the right success metrics for your organization. When it comes to sales enablement, you might ask questions like, how does content impact our opportunity creation rate? Or, what content has been used to close our biggest deals? By tracking what’s happening in the sales funnel, you can produce more of the content that drives bottom-line results and waste fewer resources on content that doesn’t.

The last thing I’ll say is CMOs really need to focus on tracking the right metrics, not just more of them. I see far too many struggle with data collection and analysis, mostly because they think they need to track everything–even metrics that don’t matter to their business at a given point in time. Analytics as a practice is where the statement “more isn’t always more” is particularly applicable.

MTS: With an exploding B2B sales tech landscape, what are the major opportunities and challenges for CMOs to meet changing definitions of personalization and customer experience?
I think the real opportunity with personalization comes when you bake in customer experience from the very beginning. That is, you use personalized elements – and research or enrichment data – to have meaningful conversations with prospects from the very first touch. And, of course, personalization here goes far beyond just adding custom variables to an automated email.

Here’s an example: Let’s say your prospect downloads a report from your website, and you notice that she spends far more time viewing the page on content performance than any other page. You can go beyond basic personalization by following up with a guide that outlines specific content KPIs and how to track them.

The challenge, of course, is implementing personalization at scale. But the nice thing about practicing Account-Based Marketing (ABM) or Account-Based Sales (ABS), which I mentioned earlier, is that you only have do it for high-value target accounts. When done correctly, personalization can help you break through the noise, and there’s a lot of it, to deliver the value that’s so integral to creating memorable customer experiences today.

MTS: What startups are you watching/keen on right now?
There are so many interesting startups getting traction today. Textio and Homebase are two that come to mind immediately. Textio is using machine learning to make job postings more effective, which is a really tangible application of that technology. Homebase is tackling the spreadsheets that are used to manage hourly employee schedules. That’s a market that’s been very resistant (so far) to change.

One more I’ve got my eye on — LaunchDarkly has implemented a service similar to an internal tool we had at Facebook. They give companies more control over roll-outs and testing for new features and deployments. I’m excited to see what’s in store for the future.

MTS: What tools does your marketing stack consist of in 2017?
We rely on a number of tools to power our marketing and sales funnels. We use Salesforce for our CRM, WordPress for our CMS, Google Analytics for site analytics, Autopilot for marketing automation, Asana for project management, and Drift for live chat.

And, of course, we use DocSend to share and track our sales content. Our sellers get to have smarter, more targeted conversations with prospects, and our marketing team gets insight into what’s actually driving the sales cycle.

MTS: Would you tell us about your standout digital campaign? (Who was your target audience and how did you measure success?)
Since DocSend is a sales content tool, we’ve always put content at the center of our digital campaigns and marketing efforts, particularly when it’s extremely useful and valuable to our target audience. We’ve had tremendous success partnering with academic institutions to deliver broader insights related to the business challenges we write about, like when we published our analysis of over 200 pitch decks with Harvard Business School.

Since we had so much success with that campaign, we decided to partner with Harvard again on our latest research report, which analyzes over 34 million interactions with sales content on DocSend. We made some interesting discoveries about the types of content sales prospects consume most often, as well as the best time to send. We measured success by downloads of the report and traffic to our landing page and blog, and we’ve crushed almost all of the goals we set for ourselves. It’s clear that sales teams are hungry for this type of information, and want to make their sales process more efficient.

MTS: How do you prepare for an AI-centric world as a marketing leader?
AI is a term that’s thrown around liberally these days. A truly AI-centric world is quite a ways off, but, in the meantime, we can leverage technology to automate a broad swath of the marketing activities we complete on a daily basis. For example, instead of wondering which sales content works best for a particular business vertical, we’ll one day be able to surface it automatically in DocSend, and use it in our sales flow to drive conversions and close more deals. We have a long way to go before we can say we live in an AI-centric world, but we’re making incredible advances in terms of making marketing easier and more scalable.

This Is How I Work

MTS: One word that best describes how you work.
Efficiently. There are only so many hours in a day. I have to work on only the most important projects and make sure I don’t get bogged down in the weeds for too long.

MTS: What apps/software/tools can’t you live without?
My shortlist: DocSend (of course), and then Gmail, Salesforce, Rapportive, Google Sheets, LinkedIn, and Carta.

MTS: What’s your smartest work related shortcut or productivity hack?
I use followupthen to schedule email reminders. You just add your reminder as a BCC to the email, like “,” and the email thread will resurface if they haven’t responded. It helps me stay on top of my most important conversations.

MTS: What are you currently reading? (What do you read, and how do you consume information?)
Recent reads include Between the World and Me by Ta-Nehisi Coates, A Short Story of Nearly Everything by Bill Bryson, Sapiens by Yuval Noah Harari and Binti by Nnedi Okorafor.

I tend to alternate between interesting sci-fi books and nonfiction or personal development books. It keeps things varied and keeps me thinking about different topics. Reading is how I take a break from thinking about DocSend all the time, and how I sneak in a little down time.

MTS: What’s the best advice you’ve ever received?
The best advice I’ve ever received is that discipline can overcome a lot of what life throws at you. It came from my dad talking about his time in the military. He always wanted to be in a rock band, go figure, but he ended up doing 16 years in the military after going through West Point.

Now, my dad’s a civilian and a doctor in South Dakota. He often speaks about how much he learned about discipline from the military and how well that’s served him over the years. I didn’t spend time in the military, but I’ve tried to apply lessons from my dad’s service to my own life.

MTS: Tag the one person in the industry whose answers to these questions you would love to read:
Satya Nadella.

MTS: Thank you Russ! That was fun and hope to see you back on MarTech Series soon.

Prior to DocSend, Russ was a Product Manager at Facebook, where he arrived via the acquisition of his startup Russ has also held roles at Dropbox, Greystripe, and Trulia. He received a BS in Computer Engineering and an MS in Computer Science from Stanford, and an MBA from Harvard.

DocSend tells you how prospects engage with your sales material after you send it. Know when to follow up, who to follow up with, and what to focus on, enabling you to do business faster. Thousands of companies rely on DocSend every day to speed up their sales cycles and close more deals. Visit the website and sign up for free at

[mnky_heading title=”MarTech Interview Series” link=”|||”]

The MTS Martech Interview Series is a fun Q&A style chat which we really enjoy doing with martech leaders. With inspiration from Lifehacker’s How I work interviews, the MarTech Series Interviews follows a two part format On Marketing Technology, and This Is How I Work. The format was chosen because when we decided to start an interview series with the biggest and brightest minds in martech – we wanted to get insight into two areas … one – their ideas on marketing tech and two – insights into the philosophy and methods that make these leaders tick.

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