Road Warrior Radio by Lola

Road Warrior Radio by Lola header image 1

One Woman’s Unlikely Journey to Sales Management

rwr-ep10b-tweet-appleyard.jpg

Ryan talks with Amy Appleyard to discuss how theatre translates to sales, past lives, and how to sure up your processes - especially with remote workers. They discuss:

  • Amy’s transition from theater to finance and into managing B2B inside sales teams
  • The importance of one-on-one connections that are available for customers, prospects and sales offices
  • Tactics in communicating with teams in separate offices
  • The challenge of driving productivity through technology for inside salespeople
  • How Amy decided on the tech stack for inside departments
  • Career advice for job transitions

Amy Appleyard is the SVP Global Inside Sales for Carbon Black, a leading cybersecurity company that specializes in next-generation endpoint security solutions delivered via the cloud.

Prior to Carbon Black, Amy was VP Sales for LogMeIn’s Communications & Collaboration line of business, and lead teams who helped customers with technology products that enabled them to meet, market, sell and train.

Before moving into the tech sector, Amy led Staples Business Advantage’s Mid-Market Sales division; she also held positions in Finance, Strategy and Marketing at Staples. Earlier in her career, she co-founded an entertainment-based retail crafts store catering to urban, professional women, Spark Craft Studios.

Appleyard also ran her own theatrical lighting design firm, based in New York and designed productions for numerous prominent theatre and opera companies. She holds a Bachelor of Arts in Theatre from Virginia Tech and an MBA from Boston University.

About Carbon Black

Carbon Black is Transforming Security Through Big Data and Analytics in the Cloud

Growing trends in mobility and cloud have made the endpoint the new perimeter. New and emerging attacks are beating traditional defenses, and security teams are too reactive and held back by their technologies.

Carbon Black is leveraging the power of big data and analytics to solve the challenges surrounding endpoint security. With the CB Predictive Security Cloud platform, we are transforming cybersecurity to deliver a cloud-native endpoint protection platform (EPP) designed to protect against the most advanced threats.

The Theatre of Sales

 

rwr-ep10-tweet-appleyard.jpg

Ryan brings on Amy Appleyard to discuss how theatre translates to sales, past lives, and how to sure up your processes - especially with remote workers.

Amy Appleyard is the SVP Global Inside Sales for Carbon Black, a leading cybersecurity company that specializes in next-generation endpoint security solutions delivered via the cloud. Prior to Carbon Black, Amy was VP Sales for LogMeIn’s Communications & Collaboration line of business, and lead teams who helped customers with technology products that enabled them to meet, market, sell and train. Before moving into the tech sector, Amy led Staples Business Advantage’s Mid-Market Sales division; she also held positions in Finance, Strategy and Marketing at Staples.  Earlier in her career, she co-founded an entertainment-based retail crafts store catering to urban, professional women, Spark Craft Studios. She also ran her own theatrical lighting design firm, based in New York and designed productions for numerous prominent theatre and opera companies. She holds a Bachelor of Arts in Theatre from Virginia Tech and an MBA from Boston University.

Testing for Coachability

RWR-9-donlan-rogul-tweet.png

 

For the first time, Road Warrior Radio will feature not one, but two people here in person at Lola Studios.

David Donlan is the CRO over at Crayon, and Mary Rogul is his VP of Sales Strategy and Engagement. Mary and Ryan used to sit next to each other in the trenches in their days as sales reps. David was one of Ryan’s first managers and certainly one of the most influential in his career.

Now you may hear the gang reminisce a little bit about the early days at Hubspot and some of the learnings that they have tried to apply to future roles. Some of those learnings worked and a lot didn’t.

The group dives into the importance of attention to detail in your sales process and what to research and prepare for when holding a meeting.

Finally, how do these seasoned sales leaders test coachability and curiosity during the interview process? Why those answers such important harbingers for success?

 

About our guests:

Mary Rogul, VP Sales Strategy - Crayon

As VP of Sales Strategy & Engagement, Mary Rogul is responsible for driving the mid-market and enterprise sales teams for Crayon, with a focus on sales hiring, training and developing a world-class team of account executives. Mary brings to the position a successful track record of more than 20 years that includes high-profile sales leadership expertise and recognized sales achievements in the B2B high-tech, healthcare, and financial services industries. A frequent speaker and panelist for Women in Sales Leadership and Women in Tech, Mary specializes in formal development and execution of strategic alliances and programs that add significant value to the customer relationship.

Prior to joining Crayon, Mary advised most recently to global enterprises to dive deeply into platform alignment, implementing strategic software and service initiatives with Cerner Healthcare and PricewaterhouseCoopers, LLP. The major contributions within these assignments are nurturing key relationships and engendered strategic partnerships that led to a much deeper understanding and support of their overall business initiatives.

Mary joins the Crayon executive team as a HubSpot alumna (2009-2015) and was part of the Enterprise Sales Scale-Up from 2011 through the public offering in 2014.

David Donlan, CRO - Crayon

David Donlan serves as the CRO for Crayon in Boston, MA. As a sales leader, he is responsible for developing market intelligence strategies that cater to the Mid- Market, and Enterprise looking to increase their sales and top-line revenue growth.

In his first 2 years, Donlan grew Crayon from 5 beta customers to more than 3,000 paid users, $5 Million in revenue, and helped raised $18 million in venture capital. Donlan is also a TEDx speaker and frequent guest lecturer at many Colleges and Universities.

Meritocracy in Sales

lola-lolapods-roadwarriorradio-twitter-1200x675-e2-v1.png

In this episode of Road Warrior Radio, Ryan and Colum Lundt cover servant leadership, meritocracy in sales, and how the right book can shape your career.

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. 

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 the 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.

Teach, Tailor and Take Control

RWR-Steve-Mackenzie.png

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

rwr-ep7-kaylor-tweet.jpg

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!

rwr-ep6-connolly-tweet.jpg

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.

RWR-CHM-Ep-5-Tweet.png

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 Lola.com 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

Twitter-allen.png 

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.

BIO:

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

lola-lolapods-roadwarriorradio-twitter-1200x675-e3-v1.png

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.