$3.5M Raised, 6m Users Helping 47k Customers Sign Documents with HelloSign CEO Joseph Walla


In Episode #517, Nathan interviews Joseph Walla, CEO and co-founder of a San Francisco based startup, HelloSign. The company launched in 2012 and it provides the easiest way for businesses to sign and collect legally binding documents online. The idea behind HelloSign was sparked by Joseph’s first successful product alongside his co-founder, Neil O’Mara, of HelloFax. HelloFax launched in 2010 after attending the prestigious startup accelerator Y Combinator.



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Famous Five:

  • Favorite Book? – High Output Management
  • What CEO do you follow? – Bill Walsh
  • Favorite online tool? — Google Apps
  • Do you get 8 hours of sleep?— Yes
  • If you could let your 20-year old self, know one thing, what would it be? – Joseph wished he had moved to the valley earlier

Time Stamped Show Notes:

  • 01:40 – Nathan introduces Joseph to the show
  • 02:30 – Joseph first worked in HelloFax which is an on-the-go fax machine
  • 02:43 – HelloSign has premium products and free products
  • 03:00 – Pricing plans starts at $15
    • 03:12 – API pricing plans differs by bucket
  • 03:40 – HelloSign is cash flow positive in 2014 and 2015
  • 03:50 – Total of $3.5M raised
  • 04:24 – Joseph has been very disciplined with how they spend their money
  • 05:15 – 2016 MRR
  • 05:36 – HelloSign has 47,000 paying customers
  • 05:46 – HelloSign has a 5-6M user base
  • 06:05 – People convert from free to paid because of the volume of their transactions
  • 06:54 – HelloSign team’s operation
  • 07:30 – Average salaries in the valley
  • 08:45 – Total headcount expenses with 16 employees
  • 09:35 – Average MRR from Nathan
  • 10:00 – Average customer churn
  • 10:55 – HelloSign is mainly in the SMB space but they also have some big clients
  • 12:20 – Standard gross churn
  • 12:40 – The amount HelloSign is willing to spend for a new user
  • 12:49 – HelloSign doesn’t spend much for a new user, but spends for a new paid user
  • 12:55 – Joseph read an article on ForEntrepreneurs.com about SaaS metrics and acquiring customers that was beneficial for him
  • 13:35 – HelloSign’s CAC ratio
  • 14:53 – Connect with Joseph through LinkedIn and Twitter
  • 16:23 – The Famous Five

3 Key Points:

  1. Don’t wait for a job or overcomplicate the process of getting started—get out there and figure it out as you go.
  2. Make that investment to turn a new user into a paid new user.
  3. Don’t just sit and wait for something to happen, take action!

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
  • @JosephWalla – Joseph’s Twitter handle
  • LinkedIn – Joseph’s LinkedIn account
  • Show Notes provided by Mallard Creatives