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 Pursuit.com. 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.

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:

• Focusing on growth rather than revenue is never bad thing.
• Improve your product until you are no longer expendable to your customers.
• 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