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

EP 581: DocSend $11M Raised, 2800+ Company Customers, 10,000+ Seats Because Links > Attachments For Docs with CEO Russ Heddleston

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