Sales Strategy Experts: Outstanding Sales Influencers You’d Want to Know | Series 2

Abhishikha Chatterjee
June 14, 2022
 mins read

Last modified on

June 14, 2022
Table of Content:

The last time we introduced 10 sales influencers through this series, our website, Convin, experienced a sudden traffic spike.

On closely watching the trend, we realized that all sales professionals are looking for solutions to their day-to-day challenges from their “heroes.”

SDRs and AEs are usually too busy to search for a Hero, someone they can look up to. Sadly, the Heroes (sales experts and influencers) are too occupied to sit down with each salesperson one-on-one.

Podcasts are the best channels to share useful information between the sales experts and the budding salespeople. 

So, we decided to make your work easier and filter the Sales Gambit podcast episodes for you. 

We will keep releasing sales influencer series frequently so you can add value to your sales strategy.

Today, we will be talking about:

  1. The Perfect Bridge Between Sales and Marketing: Michael Phelan
  2. Making Cold Calling Easy and Tactical: Risa Khamsi
  3. A Determined Sales Training Guru: Meghann Misiak.
  4. The Teacher Turned Sales Professional: Patrick William Joyce.
  5. Our Sales Technology Expert: Kellen Casebeer

1. The Perfect Bridge Between Sales and Marketing: Michael Phelan

“What I'm encouraging sales and marketing people is to spend on programs that directly generate meetings. Don't spend on programs that generate downloads, and this is what most marketers do, unfortunately.”- Michael Phelan

Michael’s the best example of a sales veteran who’s spent over 30 years in sales and marketing. He started in sales and sales management roles and transitioned to business unit management and marketing and product development–played an important role in Reebok, Polaroid, and Staples. 

For the last 10 years, he’s devoted his time to tech companies building new innovative solutions.

Michael is the Founder of Go-to-Market Pros and works with the vision of helping companies adopt & execute best-in-class programs to uncover customer insights & drive revenue opportunities.

Ashish and Michael discuss several unique cases about B2B prospect meetings. You’ll love to hear about his industry experiences. Here’s a quick inside view into an interesting discussion:

He touches upon how B2B prospecting can be more programmatic- buyer-centric and data-driven. To display the difficulties BDRs are facing in the prospecting world, he discusses the repercussions of remote working and what it does to sales meetings. Don’t miss the discussion on the referral program Mckinsey runs. You may land some brilliant ideas there.

What makes Michael’s discussion even more powerful is introducing charities to get prospects on a research call or feedback session. Prospects connect emotionally when they know their action helped a charity. You need to hear that!

And anyone facing challenges with identifying prospect channels, Michael has some brilliant ideas and experiences to share. 

Reading Recommendation from Michael’s sales library:

  1. Forbes
  2. Harvard Business Review 
  3. INC.
  4. Modern Sales Pros

“In march of 2020, when Covid-19 kind of became a big thing, I lost both of my jobs overnight and thought to myself–All right, I can sit here and feel sorry for myself, or I can learn a new skill. That's when I did a Tech Sales Bootcamp.” - Risa Khamsi

How many times have you met someone serving pastries only a couple of years and now an account executive in tech sales? 

This inspiring sales expert is none other than Risa Khamsi. 

She specializes in software sales, and apart from being an SDR(recently promoted as Account Executive at Stack Overflow), she also loves mentoring SDRs and rescuing stray cats. What an incredible thing to do?

She’s touched on a sensitive and debatable topic in the Sales Gambit Episode- How Not To Fail When Cold Calling C-suite Executives?

Here’s a short glimpse of her message for today’s sellers:

C-suite is a difficult persona to chase, but Risa has some simple yet effective ways to get to the senior execs. She captures:

As there’s no shortcut to reaching the C-suite executives, her views on how to reach the C-suite executive are practical and full of value.  But when it comes to social media and reaching the higher-ups, there’s a new perspective that needs your attention. 

Also, we are totally in love with the tone and approach she suggests to reaching out to senior leaders. What do you think it should be? Professional or Personal? Well, hear her out. 

Another practical suggestion given by Risa is to counter one of the most annoying objections- Right now is really not a good time to speak. What do you think you’d do before discovering what Risa does?

This is just one objection Risa offers a fantastic solution on; there are tons of objections she’s addressing on the podcast. 

Reading Recommendation from Risa’s sales library:

  1. The Challenger Rep By Mathew Dixon and Brent Adamson
  2. Magic by Rhonda Byrne

“Sales training is often done only to excite the sellers about their job and motivate them.” - Meghann Misiak

Meghann, unlike many sellers out there, heard her calling at the age of 16 when she took her first sales job at the retail store (yeah, that after school job.) 

She continued working in the sales industry–later as a leasing agent and worked in commission-based roles. 

Her major experience in sales started when she landed a SaaS sales role only to find ambiguity amongst senior sellers on the reasons behind success factors. She initiated a program with her senior management to learn sales training and add value to the sales team by playing the player-coach enablement role. 

Today, she's on a mission to help sellers accomplish their dreams and is dedicated to assisting them in finding meaning in sales. Meghann has been extensively contributing to sales and sales training, and she’s the founder of The Path to President's Club. You can find her on the Rev Genius community, sharing her valuable experiences. 

On the Sales Gambit episode with Ashish, she’s given a practical walkthrough of why, when, and how sales training should be executed. Here’s a short glimpse into the discussion:

The episode captures sales training in a few different scenarios:

Meghann’s explanation of how one should conclude investing in sales training is pragmatic and reasonable. She stresses being goal-oriented when it comes to choosing sales training or software.

She also wants to help sales leaders understand how much leaders should focus on each sales initiative or program. As per Meghann, sales conversations must be recorded and analyzed on Conversation Intelligence software to give product and marketing teams feedback. 

One piece of advice that every sales trainer and organization should take away from Meghann is how to ensure the skeptics are onboard and actively participate in the training program? She discusses the exact problem and the most effective solution to handle this crisis. 

Sales leaders struggling to understand if their small businesses or startups need sales training or not, Meghann has something for you. 

Recommended Read: How do start-ups train their sales team without focusing on a big training budget?

But the best part of Meghann's conversation is on how sales technology like training software isn’t going to replace trainers and coaches. You need to hear that!

Reading recommendations from Meghann’s sales library:

  1. Never Split The Difference by Chris Voss, Tahl Razz
  2. The Art Of Impossible By Stephen Cutler

“Pitfalls that I see is that the sales rep ends up trying to convince prospects of the whole kit and caboodle on the first touch, whereas all you really need to do is make the other person the other end of the line 51 sure that you might be able to help them and you've nailed some kind of a problem that they're actually trying to solve.” - Patrick William Joyce

Sales is just another number game that Patrick Joyce decided to choose after majoring in Math in undergrad and working as a High School Math Teacher. Interesting, right? 

The most exciting thing about his journey from a math teacher to a seller was that he learned the sales skills such as presentation skills, data analysis, building connections, handling objections, and ample sales skills while working as a school teacher. 

Patrick started his serious sales career as an SDR in a tech company where he stood out for his age. Patrick never looked back; he’s relentlessly contributed to sales and GTM planning. 

Today, Patrick is the VP of R&D at TIDAL and Principal at PWJ Consultancy.

Patrick’s journey and advice on the importance of right messaging for sellers are worth listening to. He’s elaborated and justified each question thoroughly. And we love it! 

Here's a brief look at the episode.

Right messaging to move stalled deals covers many facets of sales strategy, including

Patrick’s understanding of the customer and the inbound and outbound sales strategies concerning the messaging is impressive. 

He’s a practical and straightforward salesman who believes that sellers must figure out ways to help their prospects to achieve their goals and outcomes. He stresses searching for potential customers facing latent pain and helping them.

He points out that messaging that stresses the vendor's company, product, and features never works. He guides beautifully through what sellers need to change about their messaging?

  • One, push outcomes instead of features. 
  • Second, he stresses stories from current customers and the customer success teams. 

That’s what gives the right messaging. 

We are rooting on his storytelling skill and how he’s applied it in his sales game. Definitely, something to learn from Patrick. We learned a great deal from Patrick on tweaking messaging on different communication channels. 

Reading recommendations from Patrick’s sales library:

  1. Tech-powered sales by Harper Collins, Tony Hughes
  2. Zig Ziglar's Secrets of Closing the Sale by Zig Zagler

“Technology makes a lot of improvements to quantity, but not many of them improve quality. If you want to book more meetings, you must press on quality.”- Kellen Casebeer.

Want to know a more atypical sales journey? Knowing Kellen will be a great choice. 

Kellen’s sales journey started at five years of age. No kidding! Kellen had a simple question for his dad(as simple as you can expect from a 5-year-old…LOL)

Kellen: Dad, What's the job where you make a lot of money?

Kellen’s father: There's one job where you choose how much you make. In sales, the better you get and the harder you work, you can make more money. 

In college, Kellen started his sales journey with a gym membership. After graduation, he landed a sales job as an SDR in enterprise cybersecurity. Today, Kellen Casebeer is Chief of Staff at LEON Health Science. 

What an inspiring journey, isn’t it?

Kellen enlightens the audience with the precious and most practical details about the right sales tech stack in the Sales Gambit episode. Here’s a quick glimpse into an exciting discussion between Ashish and Kellen.

The episode captures the following areas of choosing a sales tech stack:

The sales landscape has changed over the years, and Kellen is a living example of how sellers worked a decade back and how it has transformed today. He’ll also talk about the biggest and the most important difference; you’ll love to know that.

His conversation with Ashish touches on the importance of software and when to onboard sales software. The discussion gets even better when they try to perceive software from a loss aversion vs. ROI standpoint.

Just not software, his judgment of using outside expertise on software is also worth understanding. While the SaaS world is pressing on Free Trials, Kellen has a different theory for software trials and their impact on purchasing the software system.

Towards the end, Kellen gives out his preferred choice of software, currently in use by his team. Kellen recommends the top 3 sales tech tools if some sales teams are on a tight budget. You should listen to the unexpected reco on number 3.

Kellen rightly points out the importance of quality over quantity and presses on focusing on call quality. He says Conversation Intelligence is one of his top priorities because performing analytics on sales calls helps in improving call quality. And software like Convin adds value to the sales calls by offering better control over the conversation quality and aids in sales coaching reps.

Reading recommendations from Kellen’s library

  1. Grit by Angela Duckworth 
  2. Antifragile: Things That Gain from Disorder by Nassim Nicholas Taleb

Want to understand why Kellen mentioned conversation Intelligence? Test it out. 

Feeling energetic? 

Don’t you think their journeys are as typical as yours? These sales experts had the most modest beginning, and today, they are slaying the industry.

If you find a chunk of resemblance with the sales journey of these sales experts, first watch the full episode on Sales Gambit. Second, start following them on Linkedin and learn as much as possible. And third, take their advice and implement the ideas in your daily practice.

Today, we intentionally covered only five guest speakers to add more value. We will be releasing yet another series of outstanding sales strategy experts.

Stay tuned and watch out for excellent sales tips and advice on Sales Gambit. Signing off!!

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