
E140 - Greg Casale and Ryan Reisert: Sell More By Increasing Live Conversations With Prospects
10/02/23 • 59 min
In this episode of Tech Sales Insights, Randy Seidl interviews Greg Casale and Ryan Reisert about the importance of live conversations in sales. They discuss the metrics of conversations versus dials, the effectiveness of cold calling, and the impact of local dialers. They also emphasize the need for personalized and targeted outreach and the importance of training and skill development for successful outbound calling. Ryan shares a study from Outreach, a billion-dollar valuation company, which suggests that after 250 deliveries, a 12% top-line response can be expected when using email and LinkedIn, compared to a 20-40% connect rate when solely using cold calling. Greg emphasizes the importance of setting realistic expectations and understanding the specific connect rates for your industry and target audience. They also discuss the qualities and training needed for successful outbound calling, including the ability to stick with the process and build muscle memory. Greg highlights that competitiveness is not the only factor for success, and introverts can excel in outbound calling due to their analytical and listening skills. They also touch on the effectiveness of phone-ready leads in increasing connect rates, with Ryan explaining that their process involves identifying signals that indicate a higher likelihood of reaching prospects.
KEY TAKEAWAYS
- Live conversations are essential for sales success as they allow for meaningful interactions with prospects.
- The connect rate for cold calling is typically between 2% and 12%, depending on the industry and target audience.
- Local dialers can be effective in some cases, but the advantage has diminished over time as people have become more accustomed to receiving sales calls on their mobile phones.
- It is important to set realistic expectations for outbound calling and understand the specific connect rates for your industry and target audience.
- The qualities needed for successful outbound calling include the ability to stick with the process and build muscle memory.
- Introverts can excel in outbound calling due to their analytical and listening skills.
- Phone-ready leads can significantly increase connect rates by identifying signals that indicate a higher likelihood of reaching prospects.
QUOTES
- "Nothing converts better than a live conversation." - Ryan Reisert
- "You want to build enough of a statistical database to know what the connect rate is for your persona in a company of the size you're trying to reach." - Greg Casale
Find out more about Greg and Ryan through the links below:
- Greg Casale: https://www.linkedin.com/in/gregcasale/
- Ryan Reisert: https://www.linkedin.com/in/salesdevelopmentrepresentative/
This episode of Tech Sales Insights is brought to you by:
- Sales Community: https://www.salescommunity.com/
- Sandler: https://www.sandler.com/
In this episode of Tech Sales Insights, Randy Seidl interviews Greg Casale and Ryan Reisert about the importance of live conversations in sales. They discuss the metrics of conversations versus dials, the effectiveness of cold calling, and the impact of local dialers. They also emphasize the need for personalized and targeted outreach and the importance of training and skill development for successful outbound calling. Ryan shares a study from Outreach, a billion-dollar valuation company, which suggests that after 250 deliveries, a 12% top-line response can be expected when using email and LinkedIn, compared to a 20-40% connect rate when solely using cold calling. Greg emphasizes the importance of setting realistic expectations and understanding the specific connect rates for your industry and target audience. They also discuss the qualities and training needed for successful outbound calling, including the ability to stick with the process and build muscle memory. Greg highlights that competitiveness is not the only factor for success, and introverts can excel in outbound calling due to their analytical and listening skills. They also touch on the effectiveness of phone-ready leads in increasing connect rates, with Ryan explaining that their process involves identifying signals that indicate a higher likelihood of reaching prospects.
KEY TAKEAWAYS
- Live conversations are essential for sales success as they allow for meaningful interactions with prospects.
- The connect rate for cold calling is typically between 2% and 12%, depending on the industry and target audience.
- Local dialers can be effective in some cases, but the advantage has diminished over time as people have become more accustomed to receiving sales calls on their mobile phones.
- It is important to set realistic expectations for outbound calling and understand the specific connect rates for your industry and target audience.
- The qualities needed for successful outbound calling include the ability to stick with the process and build muscle memory.
- Introverts can excel in outbound calling due to their analytical and listening skills.
- Phone-ready leads can significantly increase connect rates by identifying signals that indicate a higher likelihood of reaching prospects.
QUOTES
- "Nothing converts better than a live conversation." - Ryan Reisert
- "You want to build enough of a statistical database to know what the connect rate is for your persona in a company of the size you're trying to reach." - Greg Casale
Find out more about Greg and Ryan through the links below:
- Greg Casale: https://www.linkedin.com/in/gregcasale/
- Ryan Reisert: https://www.linkedin.com/in/salesdevelopmentrepresentative/
This episode of Tech Sales Insights is brought to you by:
- Sales Community: https://www.salescommunity.com/
- Sandler: https://www.sandler.com/
Previous Episode

E139 - Top Mindset Habits to be Successful in this Selling Environment with Jill Harris
In this episode of Tech Sales Insights, Randy Seidl interviews Jill Harris, the VP of Sales at GoTo, to discuss how Jill leads her sales team with a growth mindset, which means embracing challenges, learning from failures, and constantly improving their skills. They also talk about how they use customer centric selling as their sales methodology, which focuses on understanding the customer’s role, problem, and solution. Jill reveals how they use GoTo as a tool to analyze their calls, get feedback, and improve their performance. She also mentions some of the latest features of gong that they love. In addition, they share some tips and insights on selling to different markets, such as American CTOs versus European CTOs, and how to find the ideal customer profile for their products. They also discuss how they generate leads through marketing campaigns, outbound calls, and partner referrals. Jill also shares some creative ways to get meetings at conferences without having a booth. This episode is full of valuable information and advice for anyone who wants to learn more about sales success in the remote work era.
KEY TAKEAWAYS
- GoTo: Remote and secure work solutions.
- Jill's career journey as a Sales rep to VP at GoTo.
- Growth mindset: Vital for sales success; coach reps accordingly.
- Customer-centric selling: Understand customer problems and solutions.
- Gong tool: Analyze calls, receive feedback, improve performance.
- Selling across borders: Build trust, rapport, solve business problems.
- Account scoring: Prioritize valuable opportunities.
- Lead generation: Marketing, outbound calls, partner referrals.
- Creative conference meetings: Without a booth.
QUOTES
- “This is our profession, and you need to get better each and every day. If you don’t keep working on your skills and constantly tweaking, you’re going to become stale.”
- “A lot of assumptions are made in sales where you think you understand the problem, but you really need to validate that with the customer and make sure that you understood it correctly.”
- “Time is money. It really is. And so you need to do it quickly. And especially for leadership, where you’re trying to quickly dive in and read the high level notes.”
- “80 percent of your revenues come from like 20 percent of your accounts and you need to find out which ones those are.”
- “At these events, people want to talk to people. And so it is only an elevator pitch, getting curious, just striking up conversation.”
Find out more about Jill Harris in the link below:
This episode of Tech Sales Insights is brought to you by:
- Sales Community: https://www.salescommunity.com/
- Sandler: https://www.sandler.com/
Next Episode

E141 - Be Effective: As a Sales Leader Being Right is Overrated with Phil Castillo
Phil Castillo is the VP of Sales for CommScope, where he oversees the Americas region. With a background in networking and technology sales, Phil has held leadership roles at companies like Cisco, Avaya, and HP. He is known for his ability to develop top talent and drive results in challenging situations.
In this episode of Tech Sales Insights, Phil shares his insights on the importance of being effective as a sales leader. He emphasizes that being right is overrated and that it's more important to focus on being effective in order to achieve success. Phil discusses the role of intent and genuine understanding in building strong customer relationships, as well as the value of quick and concise follow-ups. He also highlights the importance of embracing authenticity and avoiding blame in order to foster trust and ownership within a team.
KEY TAKEAWAYS
- Being effective is more important than being right as a sales leader.
- Genuine intent and understanding are key to building strong customer relationships.
- Quick and concise follow-ups are crucial for maintaining momentum and trust.
- Embracing authenticity and avoiding blame fosters trust and ownership within a team.
QUOTES
- "Being right is overrated. People will remember how you made them feel, not whether you were smart." - Phil Castillo
- "Divorce yourself from the outcome and focus on understanding and learning in every interaction." - Phil Castillo
Find out more about Phil Castillo through the links below:
- Greg Casale: https://www.linkedin.com/in/phcastillo/
This episode of Tech Sales Insights is brought to you by:
- Sales Community: https://www.salescommunity.com/
- Sandler: https://www.sandler.com/
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