Wrapping a Year of Coaching (110 entrepreneurs and 81 companies!)

Earlier this year, I decided to provide a free, 45 minute coaching session to 100 entrepreneurs looking to grow their business. The spirit of this project was to give back to the tech community. When possible, I tried to help minority and women entrepreneurs, as they are generally underrepresented in the startup community and are likely in a position to benefit the most from helpful advice.

Here are some stats from the project:

  • 81 companies reached out to me
  • 71 of the meetings were scheduled and delivered
  • About 110 entrepreneurs participated in these calls (some companies had 2 or 3 attendees from the founding team, most calls were single entrepreneurs)
  • 60 comments were posted on my blog

Here are some learnings and observations from the project:

  • It’s actually quite time consuming to do all these coaching meetings! I averaged two of these per week throughout the project
  • Most entrepreneurs were very prepared about the topics they wanted to discuss
  • Most entrepreneurs found out about my service randomly, mostly on Linkedin
  • Several Alchemist Accelerator companies took advantage of the coaching, thank you Ravi and Danielle for promoting!
  • A few Pear.vc companies took advantage of the coaching, thank you Pejman and Mar!
  • 15% of the founders are female
  • 25-30% of the founders are minorities
  • 20% of the founders are overseas

My “guess” on these companies’ overall chances of success is as follows:

  • 10% are going to be very successful, I have already seen some of them in the press, making progress, growing, and receiving funding.
  • 10% are going to fail, very clearly – I did suggest on a few calls to either shut down the company/idea and/or shift to a completely new direction. Those conversations were a little uncomfortable because I hate to be the bearer of bad news, but thought it was best for the entrepreneur to hear the unfiltered, candid assessment.
  • 80% are in the middle, and look promising, but are still very delicate and anything can happen.

I did receive permission from these companies to record the calls, and I am now thinking about creating a new blog with specific observations and learnings (where we redact the company name). Let me share the high level topics that folks were most interested in:

  • How to negotiate a better position and salary
  • Finding market fit
  • Deal coaching on our first big deal
  • Deal coaching on our first pilot
  • Going upmarket to the enterprise
  • Growing sales team, how to be a sales manager
  • From traction and repeat usage growth to revenue
  • Funding, sales, generalities
  • Discuss hiring VP of Sales & COO
  • Sales and product market fit
  • Increasing pipeline for mid-market and enterprise accounts
  • How to grow the sales team in a measured way
  • Selling the company or financing it
  • Go-to-market on vertical vs horizontal
  • Venture capital strategies and tactics
  • Building your executive team, scaling your company from 10 to 100 employees
  • How to address challenges around people? How to scale services business?
  • Obtaining product market fit
  • Pricing for our platform
  • Pitch feedback, business model
  • How to create a clear plan for developing and growing a company
  • How best to approach structuring your core team
  • Need some advice figuring out what I need to do (scaling teams, scaling myself, where to focus)
  • Getting your first 10 customers
  • Building a startup in the HR space; market differentiation and positioning
  • Career advice with companies/organizations doing good for women and minorities
  • Positioning for fundraising
  • Pricing packaging, selling strategies, growing company, investment consideration since we are bootstrapped
  • Establishing a consulting business and how to get those first clients
  • Getting your first 10 customers. Pricing and packaging. Hiring your first few salespeople. Raising seed round capital. Navigating the long sales cycles in HR. Early-stage oriented
  • Gaining your first sale, going from great demo –> closing the deal
  • Moving from B2C towards B2B
  • Going from 10 to 100 customers, hiring the first few sales people, building the executive & advisory team
  • Getting our first 10 customers
  • Transitioning company from B2C to B2B, assets of the B2C company have made it possible to build a B2B solution
  • Getting our first set of quality customers
  • Scale, go-to-market in the US, fundraising

Thank you Miranda for helping me keep all these meetings organized! It was quite an effort to stay on top of all of this! Nice way to wrap up 2018!

P.S. I am taking a little break from coaching for now, and focusing on my own startup.

Kris Duggan Quoted in The Atlantic

Ranked #33 Most Influential Australian Entrepreneur

Thanks to the infamous folks at Richtopia, I managed to appear on a list of top Australian entrepreneurs.

Now, I think the ranking algorithm may be a little suspect, but I’m happy to join the ranks of the Atlassian fellows (Michael and Scott, true world-class entrepreneurs), and also the likes of Murdoch.

Edit: Let’s put the list in perspective. According to the Australia Small Businss Audit of 2017, there are 3% of households with a start-up founder (“founder of a nascent firm”). And there are approximately 8M households in Australia, representing about 240,000 entrepreneurs in this market. #33 ain’t bad!

top-100-australian-entrepreneurs-power-list-badge-richtopia.png

Mention on intelligenthq.com

Yours truly on Sales Qualia podcast

I recently had the chance to sit down with Scott Sambucci from SalesQualia on his Startup Selling Podcast to chat a bit about how startup founders be more effective and intentional in their sales approach, not to mention how to avoid some of the mistakes that I’ve made and seen countless others make over the years.

We talked about:

  • Negotiation tactics – how to get your prospects to tell you what needs to happen to get the deal done
  • Designing a pricing strategy that means no churn
  • How much Startup CEO’s need to sell before they should even consider hiring their first sales person

We also discuss some highlights from my career including: starting my own companies, raising a $100M+ in capital, what I’ve learned from interviewing over 1,000 sales people and how to manage sales teams with large targets. #nopressure

This was a fun conversation and there’s are a ton of value shared throughout the episode – so if you’re a sales oriented founder – or if you’re not – hopefully this episode will convince you of the importance of putting as much effort into your selling as you do into building you product.

You can listen to the podcast on the SalesQualia website here.

You can also follow The Startup Selling Podcast on iTunes where you can find our episode, along with a lot of other episodes that offer great sales advice:

https://itunes.apple.com/us/podcast/the-sales-podcast/id1044359904?mt=2

Check it out and let me know what you learned and what kind of questions it brought up for you so we can start our own discussion…

Workplace Trends

Live, Personalized Advice for 100 Entrepreneurs – How can I help?

I have decided that one of my 2018 goals is to help 100 entrepreneurs.

I’ll try to make myself available for any entrepreneur, even internationally. That being said, my priority is to focus on minority and women entrepreneurs, as they are generally underrepresented in the startup community and are likely in a position to benefit the most from helpful advice.

The types of companies I am probably in a position best to assist are B2B (business to business) software companies. These are companies that sell their software, typically on a subscription basis, to other businesses. My specialty is more around mid-market and Fortune 1000 types of target customer profiles, and less so on no-touch/self-serve types of customers.

My qualifications include:

  • Formally advised multiple companies in the past on go-to-market strategies, including Palantir, RelateIQ (acquired by Salesforce.com), Addepar, and others
  • Started two venture backed companies that have raised around $100M in combined capital
  • Ran the worldwide sales function for multiple organizations including carrying a $25M team sales quota
  • Personally met with 50% of the Fortune 1000
  • Interviewed about 1,000 sales people in the last 20 years
  • Hired 15 senior executives in the last 10 years

Topics I can usually help with include:

  • Getting your first 10 customers
  • Growing from 10 to 100 customers
  • Ideal customer profiles
  • Pricing and packaging
  • Deal negotiation
  • Hiring your first few sales people
  • Selling methodology and process
  • Venture capital strategies and tactics
  • Building your executive team
  • Executive compensation
  • Scaling your company from 10 to 100 employees
  • Building company brand and thought leadership
  • Goals and metrics
  • Company culture and values
  • Board communication

I think the best format for this work will be a 45 minute call, where we dive right into problem areas or issues you are dealing with. I will try to be as helpful as possible.

This “service” if you can call it that is entirely free. I am not looking for advising roles or anything beyond our initial call, as I unfortunately do not have time to do that. Now, they do say advice is worth what you pay for it. So keep that in mind…

I realize that starting a company is extraordinarily hard, and if I can even provide a little bit of help, even as a sounding board, it may ease some of the challenge in building your own business. That is not to say that I have all the answers, in fact, I am still learning every single day myself.

The only thing I ask for in return is that you comment on this page after I’ve provided my time and advice, and ideally mention the 1-2 areas that we focused on, so that I can keep track of hitting my goal of 100 conversations this year.

Ideamensch: Kris Duggan Interview

Withdrawn and Dismissed – Kris Duggan

In July 2017, a former female employee of BetterWorks filed a harassment lawsuit against me and BetterWorks, the company I founded. At the time, it was highly publicized in the press as another example of Silicon Valley bad behavior towards women. This was the first time for me experiencing something like this in over 20 years of my professional life.

During this process, the board of directors hired a third-party independent investigator to investigate the claim.

The findings of the investigator were that “no harassment, no sexual harassment, nor any assault or sexual assault occurred”, “no discrimination occurred”, and “no company policies were violated.” Upwards of fifteen witnesses participated in the investigation.

I am relieved to say that after a very disruptive eight months, the lawsuit has been withdrawn and ultimately dismissed.

People that know me know that I care deeply about women’s issues, and that I advocate for supporting as diverse and rich an environment for driving business results as possible. I spent many years, most recently at BetterWorks, creating an open, collaborative, diverse, inclusive, respectful, considerate, and flat organization. I am proud of so many aspects of BetterWorks, including the fact that 46% of our managers are female. This is roughly double the industry average. I deeply respect women, including my wife Leah. Leah and I have committed to raising our two sons to be inclusive and respectful of all people. We are proud to see them grow up in an age where equality and sensitivity to others is paramount.

Thank you to my friends and family that supported me during this difficult time. And thank you to the numerous and wonderful female leaders with whom I’ve had the extraordinary honor to work alongside.

I have decided to move on from BetterWorks as of late 2017, in order to allow the company to flourish with new leadership and eliminate any distractions. We have hired a fantastic new CEO that will be announcing soon, whom I am very excited about.

I currently continue to serve on the company’s board of directors. I am excited about the next phase of BetterWorks 2.0…

Kris Duggan in Wired