Q1: Kindly give our readers an introduction to your business. Please include what your business is all about, in which city you are located and if you have offices in multiple locations/ cities.

Ans: Treeline is the nation’s top sales recruiting firm. The company started in March of 2001 with an exclusive focus on the recruitment of sales professionals. Headquartered in Wakefield Massachusetts, Treeline has been consistently ranked as one of the Best Places to work in MA and across the country. The company is dynamic, positively charged and very generous. For 19 years Treeline employees lived throughout New England and reported to an office everyday. Since 2020, the company has become even more dynamic, embracing a 100% virtual environment for employees to flourish across the United States and Globe.

Treeline is known for building best in class sales organizations from the ground up and has built an extensive network of sales professionals. We have personal access to hard to find talent because we have built relationships within the sales community for decades. From CRO’s to BDR’s and everyone in between, Treeline is the company to partner with.

Treeline has a commitment to delivering only Qualified, Interested and Available Sales Professionals to our clients. Our exclusive Treeline ATS helps to streamline the recruiting and hiring process for clients by offering full transparency for every candidate presented, reducing the time to hire and increasing efficiencies. Treeline has a team of seasoned professionals that are coached, mentored and trained to deploy best in class recruiting and interviewing skills to qualify talent based on our client’s needs. We do not waste time and 95% of our searches are completed within 30 days.

Treeline has changed the lives of over 3,200 sales professionals over the past 21 years. The brand loyalty and following we have created is overwhelming. As an organization, from the leadership down through the entire team, everyone at Treeline is committed to positively changing the lives of so many great sales people and helping individuals advance their careers in sales. This level of brand loyalty creates an advantage in the marketplace and Treeline is seen as the go-to organization for building and scaling sales organizations.

Our purpose is to promote the good in every person and provide an environment where we are proud of the work we do and the people we work with. Treeline lives by 4 main core values.

  1. Do What’s Right
  2. Empower People
  3. Compete to Win Everyday
  4. GRIT

We live by these core values daily and as a result have been lucky enough to build a great reputation and are thankfully supported by loyal customers.

Q2: Kindly give us a brief description about yourself (it should include your brief educational or entrepreneurial background and list some of your major achievements).

Ans: I graduated from the University of Massachusetts where I received a degree in Environmental Design with a concentration in Architecture. I spent my senior year studying abroad in Denmark and backpacking through Europe. I learned about people in different countries and found that people are inherently good. Regardless of their origin, people will help you when you are in need. I believe those experiences help me to see people through an unbiased lens and have given me an advantage in the recruiting industry.

After graduation I traveled the United States landing in Jackson Hole Wyoming. My first job out of college was at Jackson Hole Ski Corporation. With little money and lots of resourcefulness I survived and learned that I could do anything I put my mind to. I came back to Massachusetts and found my way into a recruiting firm. When I first started I was not a very good recruiter and incredibly naive. But I arrived early every day and was the last to leave every night. My competitive nature and never quit attitude helped me overcome my challenges and become the top producer and Managing Partner.

I left employment to start Treeline, a company with a goal to build a positively charged non selfish company for people to find great success. We grew slowly at first and made lots of mistakes. In time we gained a strong foothold and delivered exceptional results for our clients. In time, Treeline started getting recognized for its accomplishments and incredible culture and the company created significant momentum. Treeline has been listed by INC Magazine as a top 5000 growth company for 3 years, a best place to work in Massachusetts for 8 years and one of the best places to work in the United States for 5 years by Inc Magazine. Growing Treeline from a grassroots organization to the company it is today has been one of the major achievements in my life.

Q3: What inspired you to (start a new business venture) or (to make significant changes in an existing business)? How did the idea for your business come about?

Ans: I grew up in an entrepreneurial family. My dad owned a small monogramming company in Boston and he taught me about work ethic, empathy and to always do what’s right. Time spent with dad was often going to work with him on a Saturday. That was fine by me. I was always a hard worker and time together with dad was always a great thing. Since that time I have always considered work a positive and always a fun thing for me. Work can be hard but it’s your choice to make your work world class and fun.

Q4: What three pieces of advice would you give to budding entrepreneurs?


  1. Learn the difference between Failing and Failure. Failing is a good thing because you are trying new things and you can learn from your mistakes. Failure is the result of not learning from your mistakes and giving up.
  1. Leadership is doing the right thing when no one is looking.
  1. You are an employee like everyone else. I think you need to be humble, honest and hungry to be a successful entrepreneur.

Q5: What would you say are the top three skills needed to be a successful entrepreneur?


  1. Leadership
  2. GRIT
  3. Empathy

Q6: How many hours do you work a day on average?

Ans: 9 hours

Q7: To what do you most attribute your success?

Ans: The ability to positively motivate, have fun and build a belief system of success.

Q8: How do you go about marketing your business? What has been your most successful form of marketing?

Ans: We have tried so many different marketing strategies. Because marketing is evolving and the market continues to change I can only answer this question based on our experiences now. Presently SEO is the most successful form of marketing combined with Social Brand and supportive content.

As mentioned before, we have an incredible reach in the sales community and strong brand loyalty which allows our business to thrive on referrals. Creating lasting relationships by doing what’s right is at the core of what we do so it’s natural for us to continue to build momentum and drive sales through referrals.

Q9: Where did your organizations funding/capital come from and how did you go about getting it? How did you obtain investors for your venture?

Ans: The company has no investors and has always been bootstrapped. As a result we are fiscally responsible. There is no one bailing out Treeline so we have to be very smart with every dollar we spend and decision we make. Luckily we have done a great job for the past 21 years.

Q10: What is the best way to achieve long-term success?

Ans: Hire incredible people that are not selfish and work hard for a common goal to build a company they love and are invested in. Have honest dialog where everyone can speak openly to make the company better. Always be generous and fair. Leadership is doing the right thing when no one is looking.

Q11: Where you see yourself and your business in 5 – 10 years?

Ans: We have a lot to do and our executive team has a lot of fuel in the tank to continue to grow. We constantly work on the business to make it better. Presently we are enhancing our software to revolutionize the industry and more importantly give us a substantial advantage over the competition. Our ultimate goal in 10 years is to be recognized as the global leader in sales recruiting.

Q12: Excluding yours, what company or business do you admire the most?

Ans: Amazon.

Q13: How important have good employees been to your success?

Ans: It is the most important piece to our success. We are adamant about hiring based on our core values to keep the moral and spirit of the organization healthy. Having a solid foundation made up of reliable employees all striving towards the same goals has been instrumental to our success. We have been recognized as a Best Place to Work in Massachusetts and across the country more than a dozen times and are so proud of our team and culture.

Q14: How long do you stick with an idea before giving up?

Ans: When we have a great idea we stick with it for a long time. We are great at failing and making mistakes but we are adaptable and make changes along the way. We don’t give up on an idea but instead continue to tweak and change it until we have a working solution for our clients. If an idea is clearly not going to work, we eliminate it immediately and work on other more promising ideas.

Q15: What motivates you?

Ans: The idea that we can build something better than anyone else. The challenge of running a business while disrupting the norm. Competing with other companies to be the best.

Q16: What are your ideals?

Ans: Always do the right thing. Be a great person and have no regrets. Be happy and positive and teach others to do the same.

Q17: How do you generate new ideas?

Ans: We are always keeping a pulse on the recruiting industry and what’s important to both organizations as they hire, and candidates as they evaluate the market. We do monthly brainstorming sessions around trends, opportunities, strengths and threats to our business.

To stay fresh internally, we poll our employees quarterly on what they are seeing in the market, what they would like to see Treeline start, stop and keep doing. We also have a weekly team-based huddle to discuss what we’re hearing in the market, challenges we’re facing and how to overcome them.

Q18: How do you define success?

Ans: I define success by having happy customers, happy employees and a happy family. Growing a profitable company from a professional standpoint is also how I define success.

Q19: How do you build a successful customer base?

Ans: By delivering exceptional service and doing the right thing you will build a base of repeat customers who also refer your business to their colleagues and counterparts.

Q20: What is your favorite aspect of being an entrepreneur?

Ans: The ability to think creatively and use your drive and commitment to make ideas work. There are so many bumps in the road when running a business but the challenge of making a business successful is very satisfying.

Q21: What has been your most satisfying moment in business?

Ans: The first time Treeline was recognized as the number 1 best place to work in Massachusetts.

Q22: What do you feel is the major difference between entrepreneurs and those who work for someone else?

Ans: I think the main difference is that entrepreneurs believe in something so strongly that they are able to sacrifice to accomplish their goals. I think the challenge for most entrepreneurs is to find that equal balance to satisfy both their work and personal life.

Q23: What kind of culture exists in your organization? How did you establish this tone and why did you institute this particular type of culture?

Ans: We have a positively charged culture that embraces and believes in our company and what we are trying to accomplish.

Our Purpose: WE PROMOTE THE GOOD IN EVERY PERSON and provide an environment where we are proud of the work we do and the people we work with.

Our Core Values:

  1. Do What’s Right
  2. Empower People
  3. Compete to Win Everyday
  4. GRIT

We believe in living our core values everyday and this helps to support our culture.

Q24: In one word, characterize your life as an entrepreneur?

Ans: Exciting.

Q25: If you had the chance to start your career over again, what would you do differently?

Ans: I would start a business with a recurring revenue model.

Q26: How has being an entrepreneur affected your family life?

Ans: Being an entrepreneur flows into your family. It all kind of gels together and your kids learn by example. They grow up in an environment where they are constantly learning.

Q27: What is your greatest fear, and how do you manage fear?

Ans: This may be off point, but I don’t have a greatest fear professionally. Personally I do, and that would be to lose my wife because of unforeseen circumstances. We have such a great relationship and a solid family that scenario would be unimaginable.

Q28: How did you decide on the location for your business?

Ans: Treeline originally started in Wakefield, MA and that is still our headquarters but we have no office and are 100% virtual. I chose Wakefield because when we first got started I worked crazy hours and needed to keep my commute to a minimum. I also wanted to be in a location to attract strong employees.

Since we have moved to a virtual model, we have adopted a ‘work from anywhere’ policy which has allowed our employees the flexibility and freedom to travel, spend more time with their families and experience new things. As a business owner, making this decision was not easy. I’d love to see our team more often, but now we do virtual events to have fun and plan an annual event to get together as a company.

Q29: Do you believe there is some sort of pattern or formula to becoming a successful entrepreneur?

Ans: No. Success is measured in many ways and dependent on what you consider successful. There are a lot of entrepreneurs and each may have a different idea of success.

Q30: Who has been your greatest inspiration?

Ans: My father.

Q31: What book has inspired you the most? (OR what is your favorite book?)

Ans: How to win friends and influence people. We ask everyone at the company to read it.

Q32: How can you prevent mistakes or do damage control?

Ans: It’s important to make mistakes so you can learn from them. If you find you or someone on your team is consistently making the same mistakes and it’s hurting the business/the brand, it’s important to be held accountable and figure out a way to remedy the situation. Finding coach able talent that wants to work hard, learn from mistakes, and strive to do better is the best you can ask for.

Q33: What are your hobbies? What do you do in your non-work time?

Ans: Skiing, snowmobiling, spending time with family, being on the lake, my kids have crazy sports schedules so being able to make it to their games is important too.

Q34: What makes you happy?

Ans: My family, my friends and my work.

Q35: What sacrifices have you had to make to be a successful entrepreneur?

Ans: When the company and my family were both young I needed to spend many hours away from home to make the company a success. Getting a company off the ground takes time and unfortunately that time has to come from somewhere.

Q36: If you were conducting this interview, what question would you ask?

Ans: We ask candidates about our core values and if they share the same values. This is important to make sure we hire people who believe in the same values but also to help them find success in our organization. When we do talent assessments we assess our employees on their production but also their ability to live our core values. One of our values is Do What’s Right. So an example of one of the questions we ask is whether a candidate has ever parked in a handicap spot. We have other questions around GRIT, Empowerment and Competing to win everyday.