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Teach, Tailor and Take Control


Salespeople are now teaching because the buyers already have done research. A salesperson needs to add value. Otherwise, they are relegated to being walking catalogs, and who needs another one of those?

What does my sales process look like? Do you need more leads? Stop asking the dumb questions.

Wouldn't it be better if you opened with, "Hey Steve, I've spoken to a hundred people just like you in your same position, and some of the challenges I've heard people are this, this and this. Do any of these resonate with you?"  take it further, "These are some of the solutions people have come to in order to try to solve some of those challenges."

Suddenly you are someone of interest to that prospect. This is only a taste of what is covered in this episode. Tune in to hear all the ideas and solutions.

About our guest:

Experienced Member Of The Board Of Advisors with a demonstrated history of working in the computer software industry. Skilled in Enterprise Software, Sales, Customer Relationship Management (CRM), Go-to-market Strategy, and Sales Management. Strong entrepreneurship professional with an MBA focused on Finance / Entrepreneurship from the University of Cape Town.

Todd M. Kaylor: You Have Permission to Tell on Yourself


Todd Kaylor talks about talent acquisition, people-development, and boiling things down to learn more about candidates. How do candidates fail? How do they recover? Do current employees enjoy collaborating with candidates while they’re in the office? For Todd, It’s not all about who finishes first. Check out this episode to learn how to be authentic as an interviewee and strategic as an interviewer.

About our guest:

Todd Kaylor, Director of Talent Acquisition at LogMeIn, has 20 years’ of experience in Sourcing, Talent Acquisition, and Talent Acquisition Management including stints in the Network Consulting, Staffing, Finance, Environmental, and Software industries. Todd currently manages a global team of 10 recruiters responsible for technical hiring at LogMeIn while also running the Executive Recruitment Program and In-Factor Evaluation Process. He enjoys boxing, weight lifting, baseball, watching sports and movies, and has an unusually strong, if borderline questionable, affinity for Captain America.

Mike Connolly - I want to measure everything!


Mike talks about the value of being persuasive with words and data. You don’t have to be the “Alec Baldwin” type to sell and close. Mike and Ryan dig into the traits that make a successful sales team member and how leaders can cultivate those traits to add rocket fuel to a person’s career.

About Mike Connolly:

Mike Connolly is the VP of Sales and Customer Success at CarGurus. He built and leads a team of 180 sales and service professionals, and is responsible for the revenue growth and customer satisfaction of the US customer base and helping the company execute on its mission of building the world’s most trusted and transparent automotive marketplace. Prior to CarGurus Mike led top-performing teams at Experian and Windstream, exceeding all revenue targets while maintaining a strong focus on the personal and professional development of his teams.


Cheryl Horner McDonough: No One Knows What You Want Unless You Tell Them.


Through her work creating documentaries for MTV, Nat Geo, and Netflix, Cheryl Horner McDonough has learned some important lessons about creating the career you want. As she puts it: “There’s no career fairy godmother.” If you want something, you need to speak up and make it happen. In this episode of Road Warrior Radio, Cheryl joins Sales VP Ryan L. Ball to talk about taking risks, asking for what you want and, of course, her life on the road.

Cheryl Horner McDonough is a two-time Emmy Award winner for her work on MTV’s youth-oriented True Life series and the documentary special Laverne Cox Presents: The T Word. She received a third Emmy nomination for her independent documentary film "Bean."

Cheryl is the recipient of multiple PRISM awards for documentary specials about drug addiction, two Front Page Awards, and a Peabody Award for her work on an MTV sexual health campaign.

In 2001 she founded Gigantic! Productions which has produced award winning documentaries, unscripted series, and news specials for 17 years.

Cheryl created the Netflix original series Marching Orders which debuted in 2018. She was the Series Director for Katie Couric’s six part Nat Geo series America Inside Out, and she is currently directing and producing a feature-length documentary film about the 2018 school shooting in Parkland, Florida.

Cheryl Horner McDonough lives in Manhattan with her husband Bart McDonough and their three teenage children.


Josh Allen: Let’s Have a Real Conversation


Josh Allen is the Chief Revenue Officer for one of the hottest SaaS companies on the planet: Drift. Chances are, if you’re in B2B and on LinkedIn, you’ve seen one of their videos. In this episode, Josh and Ryan riff about how tips and tricks don't work. Why detecting empathy is crucial in the hiring process, and how having authentic conversations can make all the difference in sales.


As CRO, Josh Allen is responsible for building and executing Drift's long term go-to-market sales strategy as the company strives to transform the way businesses buy from other businesses. He joins Drift after serving as SVP, North America Sales & Service at CarGurus (NASDAQ: CARG) where he led a team of more than 300 sales, service, and operations professionals during the company’s most expansive growth period.

Allen also spent a decade at LogMeIn (NASDAQ: LOGM), where he held a number of leadership positions, including VP of Sales for two of the company’s three business units, and helped open and expand their international headquarters in Dublin, Ireland.

Bart McDonough: The Expectation Book - Write it down, make it real


Bart McDonough joins Road Warrior Radio with a wealth of information around team building, interviewing, and much more. As the Founder and CEO if Agio, Bart paints a picture of what it's like to grow a business from 1 to 250 employees. This growth has earned Agio a listing on the Inc. 500 three times. Ryan and Bart dig deep on setting expectations. Do expectations align with reality when hiring? How can leaders develop talent for a growing business? Tune in to find out!

About our guest, Bart McDonough

Bart McDonough is CEO and Founder of Agio, a hybrid managed IT and cybersecurity services provider specializing in the financial services, health care and payments industries. Bart has deep institutional investment knowledge, with more than 20 years of experience working in cybersecurity, business development and IT management within the hedge fund industry. His core strengths are assessing, defining, advocating, and driving the adoption of risk management strategies, controls, and models that enabled organizations to advance cybersecurity resiliency while successfully complying with evolving regulatory requirements, and behavioral transformations.

Bart currently sits on the board of two cybersecurity firms, TwoSense.AI and Magnus Cloud, and has just launched his debut book, Cyber Smart: Five Habits to Protect Your Family, Money, and Identity from Cyber Criminals, in early 2019.


Colum Lundt: The Value of Servant Leadership in Sales


Colum Lundt is one of the premier sales trainers in the US today. As a hyper-performer at Sandler Training, Colum continues to set the bar on how to train and empower sales professionals. Many successful organizations have tapped Colum to add muscle to their sales arm. As a result, Colum was able to grow a two-person partnership to repeat appearances in the Inc 500 list of fastest growing companies. In this episode of Road Warrior Radio, Ryan and Colum cover servant leadership, meritocracy in sales, and how the right book can shape your career.

About our guest, Colum Lundt:

Colum Lundt is a sales executive, consultant and trainer with over 24 years’ experience in recruiting, sales and sales management. A former Marine, Colum began his professional career with Fleet Bank in both customer service and then their ‘telesales’ group. Following Fleet, Colum spent over five years in recruiting, sales and sales management for Darwin Partners helping drive the company from annual revenues of $14M to $150M over a five-year period.  During this time, he won every major award at the firm and consistently averaged 130% of goal. After Darwin (now called ‘Dextrys’), Colum worked in the sales training space for a Sandler Sales affiliate before joining Connect Global Solutions (now Welocalize) to lead sales for the East Coast. In this role, Colum personally drove a multimillion-dollar yearly quota with companies like Sun Microsystems, HP and Macromedia (Adobe). In addition to exceeding his number every quarter, Colum closed the largest deal in the company’s history.

In 2005, Colum launched BRIDGE Energy Group, a high-performance consulting and systems-integration firm focused on the Utility industry. His responsibilities included: recruiting the best and brightest from across the industry, creating infrastructure, developing key business and sales processes, building infrastructure, inside and outside sales, sales leadership, establishing partnerships, raising capital, managing operations, leading strategic initiatives and working with a fantastic group of experts to achieve a CAGR of 41% per year since inception. He also conceived and sold the first Cloud deal of its kind in the industry. BRIDGE has been recognized 5 years in a row by INC. 500/5000 Magazine as one of the fastest growing companies in America.

Since 2014, Colum has consulted with, coached and trained close to three thousand customer success and sales professionals, sales managers and executives for several of the fastest growing SW/SaaS companies in the country.

Mike Volpe: The Road Begins


Mike Volpe knows quite a bit about being on the road. Whether he’s crisscrossing the country to speak at industry events or meeting with investors, partners or customers, hardly a week goes by where Mike isn’t catching a plane somewhere. As a result, he’s built up a ton of tips and tricks for staying productive on the road (and plenty of war stories along the way). Check out the first episode of Road Warrior Radio to listen in as Ryan and Mike dive deep into productivity hacks, their favorite travel tools and so much more.

Mike Volpe is the CEO at, where he is responsible for definition and execution of the company’s strategy including customer service, marketing, sales, and operations. Previously he was CMO at Cybereason, a cybersecurity SaaS company, where he helped the company increase pipeline by 650% in a single year, and grow revenue by 5 times during his tenure. Mike was also part of the founding team at HubSpot, where he spent 8 years growing the company from 5 people to over 1,000 employees, $175m in revenue, and a successful IPO.

Mike (aka “the best marketer in Boston”) is well respected and active in the entrepreneurial community as a member of the board of directors of Validity, and as an advisor or investor in more than 30 startups. You can read more about Mike at

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