DocSend $11M Raised, 2800+ Company Customers, 10,000+ Seats Because Links > Attachments For Docs with CEO Russ Heddleston

Russ Heddleston

In Episode #581, Nathan interviews Russ Heddleston. He’s the CEO and co-founder of DocSend. Previously, he was a product manager for Facebook. He arrived at the B2B acquisition of the product Russ also had roles in Dropbox, Greystripe and Trulia. He received a BS in Computer Engineering and MS Computer Science at Stanford along with an MBA from Harvard.



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Famous Five:

  • Favorite Book? – Good to Great
  • What CEO do you follow? – Keith Krach
  • Favorite online tool? — Gmail and Slack
  • Do you get 8 hours of sleep?— Yes
  • If you could let your 20-year old self, know one thing, what would it be? – “Do things well and be patient with them—and then, they will turn out well later”

Time Stamped Show Notes:

  • 01:33 – Nathan introduces Russ to the show
  • 02:03 – Pursuit was a human resources to management referral program for employees
  • 02:22 – Russ shopped their company to Facebook
    • 02:38 – Russ explains why they made this decision
  • 03:38 – Russ was the product manager for Facebook’s pages team
  • 03:55 – Russ worked both for the brands and personalities
  • 04:15 – DocSend was launched in 2013
    • 04:24 – DocSend’s first version was made in 2010
  • 05:18 – First year revenue was zero
    • 05:27 – “We were focused on growth”
  • 05:50 – DocSend was doing something of very high value; not necessarily for a broad user base
  • 06:40 – DocSend has been approached by a hedge fund
  • 06:59 – Most salespeople are using DocSend long term
  • 07:37 – Average customer pay per month
  • 08:42 – Most deals of DocSend are outbound deals
  • 09:00 – Average enterprise prices:
    • 09:24 – The price varies from $50-90 per month
    • 09:40 – Outbound target for a team of 30 and above
    • 10:10 – Average contract value depends on the size of the company
  • 10:30 – Team size is 25 with 6 sales people
  • 10:42 – Team location is San Francisco with 1 in New York
  • 11:08 – Pricing plan was introduced a year after DocSend launched
  • 11:35 – The current number of DocSend’s paying companies
    • 11:48 – There’s a mix of logo and seat count
    • 12:04 – Average seats per company
  • 12:45 – Total number of users under paid plan
  • 13:03 – DocSend has raised capital for $10M in VC and $1M in venture debt
  • 14:03 – Venture debt was done post-series seed
  • 15:00 – Average MRR
    • 16:16 – Possible minimum average MRR
  • 17:00 – Russ shares the difference of inbound self-serve and outbound
    • 17:25 – Russ gets excited with outbound
  • 18:25 – Gross monthly customer churn
    • 19:01 – The churn for self-serve is quite high, but not for outbound
    • 19:45 – Net negative churn
  • 20:12 – The expansion would benefit the team
  • 20:38 – As the company gets bigger, the more they need DocSend
  • 20:48 – DocSend closed their last financing last year
  • 21:00 – DocSend doesn’t need to raise capital at the moment
    • 21:25 – “We don’t need to get acquired”
  • 23:00 – The Famous Five

3 Key Points:

  1. Focusing on growth rather than revenue is never bad thing.
  2. Improve your product until you are no longer expendable to your customers.
  3. Do things well and be patient with them—in time, they will turn out for the better.

Resources Mentioned:

  • Acuity Scheduling – Nathan uses Acuity to schedule his podcast interviews and appointments
  • Drip – Nathan uses Drip’s email automation platform and visual campaign builder to build his sales funnel
  • Toptal– Nathan found his development team using Toptal for his new business Send Later. He was able to keep 100% equity and didn’t have to hire a co-founder due to the quality of Toptal
  • Host Gator– The site Nathan uses to buy his domain names and hosting for the cheapest price possible.
  • Audible– Nathan uses Audible when he’s driving from Austin to San Antonio (1.5-hour drive) to listen to audio books.
  • The Top Inbox – The site Nathan uses to schedule emails to be sent later, set reminders in inbox, track opens, and follow-up with email sequences
  • Jamf – Jamf helped Nathan keep his Macbook Air 11” secure even when he left it in the airplane’s back seat pocket
  • Freshbooks – Nathan doesn’t waste time so he uses Freshbooks to send out invoices and collect his money. Get your free month NOW
  • Show Notes provided by Mallard Creatives

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