Mark O’Brien is a sales executive who has experienced business cultures over decades from Boston to Silicon Valley to Austin. His leadership lunch webinar “Sales Conversations,” centers on vital questions businesses should be asking their customers from a customer touch perspective of sales, business development, and support during these fluid and challenging times. Mark’s experience spans companies such as IBM, Okidata, and Microfocus. He can help companies scale from pre-revenue to $40 million+ in revenues.

Mark has a large sales quota and is a mentor at IncubuatorCTX, Vandegrift High School INCubator Program, and Mass Challenge. He received his B. Sc. In Economics and MIS Management, magna cum laude, from the University of Massachusetts – Boston and his MBA in International Management from IMEDE in Lausanne, Switzerland.

Having the right sales conversations at the right time is key. Mark’s leadership lunch webinar, “Sales Conversations,” centers on vital questions businesses should be asking their customers from a customer touch perspective of sales, business development and support during these fluid and challenging times.

The first question is, “Where Are You?” There are four distinct sales startup phases, beginning with the inception:

  1. $0 – $1 million (The Evangelist)
  2. $1 – $10 million (Mr. Make It Repeatable)
  3. $10 – $40 million (Ms. Go Big)
  4. $40 – 100 million (Mr. Dashboards)

Mark explains that if you start with the basics, you will go far and scale faster. Going from pre-revenue is up to you, the founder of your business. With the pandemic going on, revenue will start to get heavily affected in the 2nd quarter. You will not get a second chance to make an impression on a prospective customer. The “basics” are as follows:

  • It is not about your invention, it is about meeting customers unmet needs
    • You have to figure that out by asking them really penetrating interesting questions.
  • Tailor your 30-second commercial to the audience.
    • Investors, customers, and tech all require a different approach.
  • Play “Let’s Pretend” to overcome objections.
    • If a prospect has excuses as to why they can’t do something, pretend like it is no longer an obstacle.
  • Act like a dummy, on purpose. Get them to talk up to 80% of the time.
    • Your prospect will answer questions you ask and should talk about 80% of the time you are speaking. If you “act like a dummy,” prospects will over-explain things and that ends up helping you both.
  • Actively listen like a nurturing adult. “Interesting that you say that.”
    • Practice active listening and allow them to explain where they’re coming from. Care and try to understand what they are saying to you.
  • Don’t assume, ask interesting questions about them and their process.
    • Find out what’s important on their mind, and help them. If you can’t help them, help them find someone who can.
  • Always Give and Get in compromise.
    • Make sure they are also receiving something in an agreement and it is not just benefiting you.
  • Beware of The Information Trap and The Demo Trap.
    • “Just send me the brochure.” Make sure you follow up that brochure with a call! Always make sure you are in contact with them and don’t get trapped in a no-reply loop. A demo is not a lecture, it’s an opportunity to learn why the customer is doing the demo and what is motivating them. Why is your product going to be helpful to them?
  • Start small, but start somewhere.
    • It’s much better to have a small closed deal with a customer who’s paying then waiting for the deal to get bigger.
  • The earlier and harder you qualify, the easier the close.
    • The earlier you qualify in a process, the easier to close. With an “upfront contract” at the beginning, it makes it clear what you are there to do, and it is talk sales.

In conclusion, Mark suggests not reading too many books on sales. Instead, he personally visits the following resources for more sales insight:, Jason Lemkin (@jasonlk), Echosign/Adobe, Tomasz Tunguz, Repoint Ventures, VC Insight, Sandler Sales Methodology, Hubspot, Dharmesh Shah, and CTO Co-Founder.


Watch the questions asked here:

Affiliate Marketing Programs

  • During this question, Mark discusses affiliate marketing programs and their place within the sales world. Learn how this can affect your business with this quick video.

Sales Reps

  • During this question, Mark touches on the use of sales representatives and what your business should look for in the hiring and transition process.

Establishing Product Credibility

  • During this question, Mark discusses how to establish product credibility in your sales process to lead to more sales. Learn some quick tips from this short video!

Founders as Sales People

  • During this question, Mark touches on founders as salespeople, and when you should be making a transition to a full sales team!

Sales Funnel Setup Mistakes

  • Some of the key sales funnel setup mistakes are discussed. Learn with this quick video what some of those mistakes are and how to correctly set up your sales funnel!

First Ten Seconds of Sales

  • The first ten seconds of sales are discussed. Learn from a seasoned sales veteran Mark O’Brien how to effectively use this time to draw your customers in!

Startup Sales Hiring

  • Mark discusses what you need to look for when hiring for your startup sales team. Learn some quick tips and red flags when determining your best hire!

Pivot Point for Handing Off Sales

  • Mark speaks on when you need to pivot to a full sales team in your business. When does the profit of a full sales team start outweighing the cost?

Ventures for Predictable Revenue

  • This question discusses some ventures that produce predictable revenue!

Is Crowdfunding Still Valid?

  • Is crowdfunding still a valid option to raise funds?

How To Not Waste Time

  • We’ve all been there, a salesperson dragging on during a pitch. Learn some tips on how to not waste your time or your potential customers’ time in the sales process!



Written by Hannah Watson



About IncubatorCTX

IncubatorCTX helps startups and early-stage companies grown and succeed. Our goal is to promote innovation and impact in Northwest Austin along the HWY 620 corridor. We are located on the campus of Concordia University Texas amidst 400 acres of Hill country preserve.

IncubatorCTX members have 24/7 access to vibrant co-working space alongside other entrepreneurs. IncubatorCTX is much more than a co-working space; our members also benefit from a network of mentors, entrepreneurial programming, classes, events, and access to faculty and student workers.

For more information or to become a member, please go to or to learn more about Concordia University Texas go to