Interview with Jason O’Hare @MobileMonkey

Interview with Jason O’Hare @MobileMonkey

It’s no secret that I love meeting and connecting with new people. Whether it be someone in the industry or an elderly lady at the bus stop, I’m always down for a chat.

In the most basic sense, I love hearing stories.

This is exactly what prompted me to ask today’s guest, Jason O’Hare, if he would be interested in doing an interview for the TechWyse blog.

When it comes to building out a sales team, Jason has an incredible record of success, especially in the software startup space. Back in 2010, he joined a technology SaaS startup by the name of Wordstream as the Vice President of Sales. In the 5+ years he was there, Jason built out a world class sales team which directly contributed to Wordstream’s massive success and reputation as one of the top startups in the Boston tech scene.

Today, Jason is back at the helm leading the sales operation for a new Boston-based mobile marketing startup called Mobile Monkey.

I want to thank him for taking the time out to share some thoughts and stories with us.

Q:  In your opinion, how has the search marketing software landscape changed since 2010 when you first joined WordStream?

A:  These days Digital marketers are more savvy than just a few years ago. They didn’t teach this stuff in school in 00’s and it was still new to the majority of customers we spoke with.

In 2010 it was sort of the end of the “wild west” for paid search. The easy money was no longer there in PPC and Marketers really started to look for tools that could help them get an edge.

And of course, in 2010 Google was king.  Now in 2017, Facebook is a major player.

Q:  I've always believed that startups present a unique opportunity for individuals with leadership qualities to step up and make an impact. What are your favorite aspects of working within a start up environment compared to joining an established company?

A:  Where do I start?  I like just about everything better. I love the fast-pace, the daily problem solving, the accountability and the ability to have a great idea and get to work on it the same day.  These things are much harder the bigger an organization gets – and it’s something growing start-ups need to keep an eye on. After all, the goal is to become a big company one day.

Q:  Good Will Hunting. Yay or Nay? It's one of my personal favorites but I've always been curious if Massachusetts is like it or not.

A:  Ha!  I was living in LA when that moving came out and all of a sudden everyone thought that I must be from southie because I’m from Boston (I’m not from southie).  But to answer the question – yes, we love it.

Q:  As a VP of Sales, how big of role does motivation play when it comes to managing a multi-level sales team in the digital marketing space?

A:  Huge. Sales is hard work and sales management is even harder.  Good reps are motivated by success.  A good way to motivate Reps is to help them succeed.

Q:  What are your top 3 pieces of advice for an individual that wants to make a name for themselves in tech sales?

A:  First of all if your goal is the “make a name for yourself”, then my advice is be an actor or politician not a sales rep. If you want to be successful in Sales and make a great income then here a few things you can do.

  • Find a good product in a great big market to sell.  You want what I call a “target rich environment”.  Avoid niche products.
  • Join a startup!  Get in there, get your hands dirty and figure it out.
  • And of course –work on your craft, practice it, learn from others. Sales is like being an athlete or musician, in that it takes constant practicing and skill development.

Q:  What was it like being a high school teacher in the late 90's? Were there any experiences you had that still stick with you today?

A:  It was awesome!  I have so many stories from those years.  One that sticks with me is in my first year I had a class of really tough kids and I was frustrated because they were so much more work than my “good” students. A veteran teacher sat me down and told me the “good” students were easy, they are going to do well in life regardless of what we do.  But it’s the “tough” students that need great teachers.

Q:  In your opinion, how important is it to determine the lifetime value of the customer when it comes to successfully growing a subscription based SaaS business?

A:  Well its critical.  But in the early stages it’s hard to determine so keep an eye on monthly churn rates both in units and revenue.

Q:  Where do you see the SaaS business model heading in the next 5-10 years?

A:  More and more competitive.  Let’s face it technology is easier to build and deliver every year. “Saas” is becoming a mature model and the play book is written.  It’s all about who executes the best – who ever sells the most and provides the best service wins.

Q:  Guilty musical pleasure? It could be a band or a song. Mine would definitely be the band Toto.

A:  Grateful Dead!

Q:  How important do you feel the relationship is between the marketing and sales teams in a startup environment?

A:  In a start-up these functions should be run either by 1 person or 2 people that are 100% aligned and attached at the hip.

Q:  In your experience, what are some of the biggest factors that would cause an online business to have a higher than average churn rate?

A:  SaaS products need to grow in value over time and be painful to leave.  High churn for a SaaS product can be caused by many things:

  • Selling it to the wrong people. Watch the cohorts of who is joining. If some stand out as super high churn, stop selling to them and focus on the lowest churn groups.
  • Price is wrong. Too High, they can’t afford to stay. Too low the wrong customers may sign up!
  • Product loses value over time instead of gains value…this is an obvious one but surprising how often we see this.

Q:  If I went back in time and asked 10 year old Jason O-Hare what he wanted to be when he grew up, what would his answer have been?


Q:  Lastly, I’m a lover of all foods.. What's your favorite type of food or place to eat that’s unique to Boston?

Love New England Seafood!

Thanks again to Jason O’Hare for taking the time out to entertain my curious mind and share some of his sales expertise with our subscribers.

If you like reading interviews with top leaders in the digital space, be sure to check out the past interviews we’ve done. If there is someone you’d like to see interviewed on the TechWyse blog, be sure to leave a comment below.

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