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How the Deal was Done | Deal Stories Podcast

How the Deal was Done | Deal Stories Podcast
Author: Andrew Kappel
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How the Deal was Done | Deal Stories Podcast features fast-paced interviews with top sellers & leaders.
Insights and Inspiration.
1. You will hear the story for how a large deal was won 2. We'll cover the backstory, challenges, and learnings picked up along the way. All in about 15 minutes.
If you have questions or would like to recommend a guest please connect with Andrew Kappel on LinkedIn: https://www.linkedin.com/in/andrewkappel/
Insights and Inspiration.
1. You will hear the story for how a large deal was won 2. We'll cover the backstory, challenges, and learnings picked up along the way. All in about 15 minutes.
If you have questions or would like to recommend a guest please connect with Andrew Kappel on LinkedIn: https://www.linkedin.com/in/andrewkappel/
60 Episodes
Reverse
Chas Puleo, a senior sales executive at Alkami, shares his experience in closing a transformative $5 million deal in the digital banking space. This episode covers the challenges of resetting a deal after a key decision-maker was promoted and the importance of business cases in complex sales cycles.
Background:
Chas started his career in banking and transitioned into tech sales, currently at Alkami as a senior sales executive.
The deal took over two years, with an internal team evaluation for a digital banking platform at a financial institution.
Challenges:
Rebuilding momentum and trust after the main decision-maker was promoted.
Navigating a long, complex sales cycle while maintaining consistent engagement over two years.
Key learnings:
Building a collaborative business case with the client ensures alignment and trust.
Leveraging relationships and offering best practices can help smooth long internal evaluations.
Timestamps:
07:15 — Chas's background and entry into tech sales
12:34 — First contact and prospecting challenges
21:10 — The importance of building a champion in the client organization
24:45 — Resetting the deal after a key decision-maker was promoted
31:12 — Collaborative business cases and their importance in complex sales
40:50 — The value of integrity and avoiding negative selling
45:30 — Using imposter syndrome as a superpower
Resources:
Find Chas on LinkedIn where Chas releases his newsletter
Find Chas's art online at Chasisart.com
Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room.
Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn
As 2024 comes to a close, and sights set on 2025, Andrew discusses major life updates including his introduction to fatherhood, his growing and evolving consulting business, and the conclusion of How the Deal was Done Podcast plus what is on the horizon.Interested in developing business cases WITH your champions? Checkout Fluint to do just that. Grab a free download of their top performing sales frameworks and templates. And listen to a few How the Deal was Done eps by visiting:https://www.fluint.io/dealpodTimestamps: 02:57 Consulting & Professional Updates06:10 Future Plans and New Podcast Concept for 202509:01 Gratitude and AcknowledgmentsShoutouts:- OrgChartHub: Co-Founders Dan Currin and Austin Birch original supporter and sponsors of How the Deal was Done- Fluint: Nate Nasralla and Ben Wordell current sponsors and partners of the podcast.- Thousands of listeners including over 100+ who have How the Deal was Done as a top podcast- Brett Muni for the support as editor and now Producer of the podcast- Looking for more Sales Podcasts & Content? - checkout Scott Ingram's Sales Success Stories Podcast. https://top1.fm/all-sales-podcast-episodes/
Another special guest host episode featuring Mitchell Kasprzyk.
In this episode, Dave Brock shares his unique journey into sales, highlighting the importance of understanding customer needs and building trust. He recounts memorable deal stories, particularly focusing on a young salesperson's success through effective coaching.
The conversation emphasizes the significance of continuous learning and adapting sales strategies to meet customer expectations, ultimately leading to successful outcomes.
Timestamps:
00:00 Introduction to Sales Journey
03:57 Memorable Deal Stories
11:58 Understanding Customer Needs
20:09 Building Trust and Confidence
27:59 Continuous Learning and Adaptation
Resources:
David Brock on LinkedIn: https://www.linkedin.com/in/davebrock/
David’s blog: https://partnersinexcellenceblog.com/
David’s book: https://www.amazon.com/Sales-Manager-Survival-Guide-Lessons/dp/0997560207
Mitchell on LinkedIn: https://www.linkedin.com/in/mitchell-kasprzyk-3296b898/
Questions, comments, ideas - reach out to https://www.linkedin.com/in/andrewkappel/
In this episode of the Deal Stories podcast, Vince Beese, a seasoned sales leader with extensive background in sales, shares insights from his career, and focusing on a significant deal he closed with Yahoo.
The highlight of this deal is navigating the RFP process, the challenges faced during negotiations, and the importance of alignment and honesty in enterprise sales. Closing it out: Vince emphasizes the need for hustle, persistence, and a clear value prop when closing large deals.
Check out SalesHQ next time you are selling/visiting the Raleigh-Durham area!
Timestamps:
(00:00) Intro to Vince Beese and Sales HQ
(02:12) Cheetah Mail Deal Background
(04:24) Navigating the RFP: Telling Client What they Don't Want to Hear
(08:24) Small Startup - Challenges in Closing the Deal
(11:44) Celebrating Success and Reflections
(14:06) Key Takeaways for Enterprise Deals
Resources:
https://www.linkedin.com/in/vbeese/
https://www.saleshq.co
Questions, comments, ideas - reach out to https://www.linkedin.com/in/andrewkappel/
Chas Puleo, Senior Sales Executive at Alkami, returns to in this follow-up episode to last week's conversation (Ep. 55) to discuss the closing of a 2-year, $5 million digital banking. He highlights the importance of aligning with the client’s business needs and the role of executive involvement in moving large deals forward.
Background:
Chas has been a Senior Sales Executive at Alkami for five an years selling digital banking solutions to U.S. financial institutions.
The $5 million deal took over two years to close, involved multiple C-suite executives, and was for digital banking solutions.
Challenges:
The primary contact in the deal was promoted mid-process, requiring Chas to rebuild the relationship with a new champion from scratch.
Timing conflicts at a key conference led to difficulties in securing critical face-to-face meetings with the client.
Key learnings:
Building strong relationships based on trust and transparency is crucial for closing major deals.
Involving the C-suite early and maintaining their engagement throughout the process can greatly improve your chances of success.
Timestamps:
(01:12) Keys to success in the deal.
(03:40) Positioning yourself as a partner vs. vendor.
(06:53) Relationship building with trust and transparency.
(08:52) Importance of executive leadership involvement.
(14:45) Internal deal briefings and executive communication strategy.
(20:15) Challenges of partner vs. vendor positioning.
(26:21) Significance of texting in building client relationships.
Resources
Find Chas on LinkedIn
Checkout Run the Hills where Chas releases his newsletter
Find Chas's art online
Thank you to Fluint for Sponsoring this episode They help sellers build a business case that cvan sell for them even when they aren’t in the room.
Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn
Quick episode here. Talking a bit behind the scenes of 'how' the new Leader Leverage Podcast came to be.
You can find link to the YouTube of Ep 1 of Leader Leverage Podcast below.
Also, you can checkout the new Substack newsletter that goes along with it.
Thanks for listening and your support!
Link to Leader Leverage Podcast ep 1 now available on YouTube
Starting by handing out flyers in grocery stores, Rob DeSantis worked his way to become a world-class seller, co-founder, and angel investor.
Rob is a Co-Founder at Ariba (IPO & Acquired by SAP), early Board Member at LinkedIn, and currently a hands-on startup advisor/investor.
Sales has been at the center of his success, and in this interview, Rob shares the most memorable deal and the learnings he has picked up throughout his career.
For salespeople, Rob offers advice and tactics that have driven his unrivaled success.
For everyone, Rob shares his perspective on how to live a hard-working, happy and purpose-driven life.
For Rob, that purpose drives him to continually be a builder of companies, a competitive athlete, and a proud family man and father.
Chapter Markers:
0:00:00 - Intro
0:00:39 - Sales Origins
0:16:27 - Ariba Beginnings
0:23:49 - The $10 Million Dollar Phillips Deal
0:41:17 - Money & Time
1:03:53 - Advice
1:13:09 - Legacy
A special thank you to Gary Griffith who helped create the opportunity for us to share Rob's inspiring story.
Check out the video version of this podcast on YouTube
To learn more about How the Deal was Done Podcast - you can subscribe at www.DealStoriesPodcast.com or reach out to host Andrew Kappel on LinkedIn
Check out the Full Length Episode on YouTube where Rob shares the deal stories that standout from his illustrious career so far.
Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn
Mitchell Kaspryzk re-joins the podcast this time as a guest host featuring a discussion with renowned sales expert Andy Paul. Andy shares insights from his extensive career and delve into a challenging deal involving the development of real-time entertainment systems for commercial airplanes, highlighting the importance of trust and understanding in sales.
Background:
Andy Paul has had a long and diverse career in sales, authoring several books and hosting successful podcasts.
The deal involved selling a complex real-time entertainment system to a Fortune 500 media company, which required custom development and cost approximately $12 million.
Challenges:
The company made a critical pricing error, requiring them to double the cost at the last minute.
The deal involved creating a product that didn't yet exist, necessitating true collaboration with the buyer.
Key Learnings:
Building and maintaining trust is crucial, especially when unexpected challenges arise.
Sales success often hinges on deeply understanding the customer's needs and being adaptable in addressing them.
Timestamps:
(02:37) Andy Paul's entry into sales
(05:05) Initial connection with the big media company
(08:37) Technical challenges in developing the product
(12:21) Critical pricing error and how it was handled
(17:18) Importance of the buyer’s experience with the seller
(27:30) The value of deep understanding in sales
Resources:
Follow Mitchell Kasprzyk on LinkedIn
Follow Andy Paul on LinkedInThank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room.
Check out their solution here: fluint.io/dealpod
Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn
Ian McDonald shares a large deal, where his company first landed the initial product sale, and the process of working hard to make them into a successful multi-product and platform customer .
Background:Ian McDonald is currently an AE manager at Gong with prior sales experience, at LinkedIn and CEBIan shares a past deal including the account management tactics used to expand a customer.
Background:Covers deal setup and the process and relationship development with the AE who won the new logo and the championChallenges:Aligning customer's needs with Gong's product roadmapCoordinating with internal leadership to build trust and relationships with the customerKey Learnings:Focus on being a trusted partner to help overcome speed bumps in the deal cycleKnow the skills that you need and work backwards to develop those skills
Timestamps:(02:00) - Ian's career journey so far(03:15) - Start of the deal(05:40) - Main challenges in the deal(08:15) - Expanding the deal(10:30) - Strategies for getting better(13:50) - Connect with Ian
Resources:Connect with Ian on LinkedInLearn more about LeaderLevThank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpodQuestions, comments, ideas - reach out to: Andrew Kappel
Episode 50. Thank you for listening this far. More to come!In this episode we welcome Chris Orlob who shares his boomerang journey from seller to startup founder to SaaS sales leader and now back to startup founder. For the deal we cover a recent $110,000 win for his current startup Pclub.io
Background:Chris identifies more as an entrepreneur than a sales leader, having started his career at InsideSales.com and later founding startups like Conversature and Pclub.ioThe deal involved selling Pclub's skill transformation platform to a marketing automation company for $110,000, spanning multiple departments and requiring extensive multithreading.Challenges:Procurement demanded a significant discount, initially offering a budget far below the quoted price.Ensuring differentiation and building a strong business case to justify the higher price point against competitors.Key learnings:The importance of undeniable defensibility, including quantified value, differentiation, and powerful champions.The value of a multithreaded network and having a compelling event to anchor the negotiation timeline.Timestamps:01:02 – Chris's career journey split across being a seller, leader, and entrepreneur.03:41 – Founding Conversature and its challenges.06:24 – Overview of Pclub's skill transformation platform.08:37 – How the deal started with individual subscriptions leading to enterprise interest similar to PLG model11:03 – Challenges with procurement and the negotiation process.18:48 – Key strategy for successful negotiation: undeniable defensibility.
Resources:Find Chris Orlob on LinkedInThank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpodQuestions, comments, ideas - reach out to: Andrew Kappel
Haley Ben-Izhak shares insights into closing a significant deal with a top home care provider in the US, highlighting the challenges and strategies involved.
Background:
Haley Ben-Izhak is an enterprise & large account executive for Nevvon; she has a background in advertising sales, event marketing, and is also a business owner.
Nevvon is an online training platform for the home care industry
Challenges:
Long sales cycle over two+ years
Various starts and stops and executive turnover
Need to align with the client’s budgeting periods and fit into larger software migration a la implementation of a new CRM or ERP.
Key Learnings:
The importance of multi-threading and engaging with multiple stakeholders early in the sales process.
Using Fluint's written business case framework to improve discovery and effectively communicate the economic impact to the client.
Timestamps:
(0:02:46) Deal OverviewDetails and background about Hailey's company and the end-user client
(0:04:25) Challenges in the DealDiscussing the hurdles faced during the sales process.
(0:05:57) Integration StrategyHow Nivvon’s software integrates with the client’s systems.
(0:08:24) Champion TransitionHandling the transition of the internal champion at the client’s organization.
(0:14:09) Utilizing FluentThe impact of using Fluint's business case framework on the deal’s success.
Resources:
LinkedIn: Hailey Ben-IzhakThank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpodQuestions, comments, ideas - reach out to: Andrew Kappel
Caleb King, a founding Account Executive at Supered, discusses an unusual yet highly successful deal from his time at HubSpot, emphasizing the importance of recognizing and handling outliers in sales processes. The deal involved a large multinational company and was closed in just two weeks.
Background:
Caleb King was a channel account manager at HubSpot working with agency and consulting partners
Now, Caleb also works with HubSpot partners as a Founding Account Exec at Supered.
The deal involved a large multinational company, closed in two weeks, and accounted for 95% of Caleb's monthly quota.
Challenges:
The deal followed no traditional sales or prospecting playbooks.
Internal processes and demands for multiple meetings risked slowing down the deal.
Key Learnings:
Recognize and give special attention to outlier deals.
Build a process-driven day but remain open to the unpredictability of sales.
Timestamps:
00:56 – Caleb King's background and role at Supered02:59 – Overview of the whale deal from HubSpot04:13 – Selling through the channel and the unique company involved06:07 – Internal operations and managing risk for the deal08:24 – Key learnings from the deal and the importance of process09:49 – Relationship with the rev ops agency involved12:03 – Supered's go-to-market strategy and the concept of the dark funnel
Resources:
Find Caleb King on LinkedIn
Check out Supered
Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpod
Questions, comments, ideas - reach out to: Andrew Kappel
Mitchell Kasprzyk, VP of Sales at Compyl, shares a pivotal deal story that led to a significant funding round for his organization. His journey from opera singer to sales leader adds a unique twist to his approach and philosophy in selling.
Background:
Mitchell Kasprzyk started his career as an opera singer before transitioning to sales, now serving as VP of Sales at Compyl.
The deal involved a significant round of funding for Compyl, initiated through a first call with the CTO of a larger parent organization.
Challenges:
The CTO's initial resistance, stating he didn't want a sales pitch and wanted to see the tool directly.
Overcoming the underdog status of being a lesser-known startup in a competitive cybersecurity market.
Key learnings:
Demonstrating transparency and empathy can build trust even with initially resistant clients.
Understanding and addressing the specific business outcomes and challenges of the client is crucial.
Timestamps:
0:00:02 - Introduction and welcome
0:00:26 - Mitchell's career background
0:03:44 - Initial challenge with the CTO
0:06:11 - Networking at an industry event
0:09:34 - Developing the business case
0:15:08 - Key lessons from the deal
0:21:10 - Parallels between opera and sales
Resources:
Follow Mitchell Kasprzyk on LinkedIn
Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpod
Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn
Samantha Price shares her career journey from journalism to sales and details a recent significant deal she closed at Persefoni. She highlights the unique challenges of selling sustainability software to Fortune 500 companies and the strategies she uses to succeed.
Background:
Samantha transitioned from journalism to sales and now works at Persefoni, focusing on environmental sustainability.
She closed a sustainability software deal with a Fortune 500 company; utilizing the Fluint one-page business case to simplify the process by aligning both internal and external stakeholders.
Challenges:
Selling sustainability software to buyers unfamiliar with purchasing software.
Navigating the complexities of budget approval and competitive differentiation in a niche market.
Key learnings:
Simplifying communication and reducing friction for buyers is crucial.
Leveraging relationships and industry connections can open significant opportunities.
Timestamps:
(0:00:00) - Background of Samantha Price
(0:05:27) - Challenges in selling sustainability software
(0:07:32) - Insights on understanding buyer's needs
(0:10:50) - Strategies for simplifying communication
(0:13:19) - Success and replication of the deal
(0:14:37) - Benefits of using Fluint to create business cases with your buyers
Resources:
Follow Samantha Price on LinkedIn
Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. Check out their solution here: fluint.io/dealpod
Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn
Welcome to a special, non-traditional episode with founder Adam Robinson. His perspectives around organic/social marketing and product lead growth (PLG) have guided the success of his software startups.
B2B sellers may learn techniques from Adam's approach to improve his companies' prospecting and sales process execution.
Key Topics:
Adam's experience with building and growing his companies, including his approach to B2B sales and marketing
Adam's use of social media and content creation to drive awareness and build his personal brand
The importance of being adaptable and willing to iterate
Adam's views on the future of sales and marketing in the B2B space
Timestamps:
01:37 - Discussion on sales models and trends, including B2B vs B2C.
02:32 - Contrasting sales models for Retention.com and RB2B.
09:32 - Discussion on PLG and the feedback cycle for experiments.
11:28 - Discussion on the surprises and assumptions in the experiment.
Resources:
Follow Adam Robinson on LinkedIn
Check out Adam's Startups: RB2B and Retention.com
Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. Check out their solution here: fluint.io/dealpod
Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn
Greg Crisci discusses his unique approach to selling childcare benefits to enterprises, emphasizing the importance of storytelling and business cases. He shares a notable deal that took over 400 days to close, highlighting the challenges and key learnings from the process.
Background:
Greg is an entrepreneur at heart with a history in startups and a focus on selling products and services that make the world a better place.
The deal involved selling a childcare benefit solution to a mid-market company, primarily driven by employee resource groups and the CEO.
Challenges:
Overcoming HR's perception that childcare wasn't a problem due to lack of direct complaints.
Educating the employee resource group champion on how to present the business case effectively to executives.
Key learnings:
Building a strong narrative and concise business case can drive decisions from the top.
Engaging and educating champions within the organization can be crucial for influencing decision-makers.
Timestamps:
(0:01:12) Greg’s background and entrepreneurial journey
(0:04:25) Current role and responsibilities
(0:06:46) Explanation of the deal and the solution provided
(0:08:54) Challenges faced during the deal process
(0:12:38) Importance of a strong narrative and business case
(0:17:48) The final steps to closing the deal
Resources:
Greg's LinkedIn
Greg’s podcast
Fluint's top five frameworks
Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpod
Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn
In this episode, Scott Ingram shares his journey through a significant sales deal that not only secured a world-class client but also exemplified the power of teamwork and cultural values. Scott's experience emphasizes the importance of perseverance, client relationships, and leveraging company culture to achieve remarkable sales success.
Background:
Scott Ingram is a seasoned sales professional with over 15 years in SaaS sales, and the host of the Sales Success Stories podcast.
The deal was with a major digital camera manufacturer and was instrumental in Scott's early career success, highlighting his innovative approach to structuring deals and leveraging company culture.
Challenges:
The deal faced a critical timing issue, with only days left in the fiscal year to complete the legal review and finalize the agreement.
Scott had to convince internal stakeholders and navigate the client's internal processes to get the deal approved under a tight deadline.
Key Learnings:
The importance of a strong sales culture and rallying internal support can significantly impact the success of a deal.
Building deep, personal relationships with clients and working collaboratively can lead to long-term success and substantial lifetime value for the company.
Timestamps:
(0:01:33) – Scott Ingram's background and career overview
(0:03:30) – Introduction to the Sales Success Stories podcast
(0:04:20) – The setup of Scott’s significant deal with a digital camera manufacturer
(0:07:58) – Key challenges and cultural impacts during the deal
(0:12:19) – Scott's critical email and the turning point in the deal
(0:19:01) – Celebrating the deal and its long-term impact
(0:24:17) – Conclusion and call for top sales performers to share their stories
Resources:
Sales Success Media
Scott on LinkedIn
Scott’s Daily Sales Tip #1529 HTDWD
Evan Kelsay's Top SaaS Deal
Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell when they aren’t in the room. Check them out at fluint.io/dealpod
Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn
In this episode of "How the Deal Was Done," Jarred Knapp, an enterprise AE at SPS Commerce, shares his journey from kinesiology to sales success. He details closing a 50k ARR deal in just three weeks using Fluint to build a strong business case.
Background:
Jarred Knapp transitioned from kinesiology to sales and has been with SPS Commerce for nine years.
He closed a 50k ARR deal in three weeks by leveraging Fluint to sell compliance in the retail supply chain.
Challenges:
Navigating compliance requirements in the retail supply chain.
Building a compelling business case that stakeholders can easily understand.
Key Learnings:
The importance of creating a strong, clear business case.
Leveraging tools like Fluint to help you write a compelling business case can significantly speed up the sales process.
Timestamps:
(0:01:12) - Jarred's background and career journey
(0:03:13) - Overview of SPS Commerce and Jared's role
(0:03:26) - Introduction to the 50k ARR deal
(0:06:04) - Typical vs. accelerated sales cycles
(0:08:33) - Importance of compliance requirements
Connect with Jarred Knapp on LinkedIn
Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. Check out their solution and grab the top 5 frameworks by visiting https://www.fluint.io/dealpod
Questions, comments, or future guest recommendations- reach out to Andrew Kappel on LinkedIn
In this episode of "How the Deal Was Done," Andrew Kappel and Bijay Alex Mathew discuss a major deal with a leading athleisure retailer facilitated through a key partnership. They explore the challenges faced with outdated software and how over-servicing and strong partnerships played a role in closing the deal.
Background:
Bijay has 20 years of experience leading sales teams and currently serves as the CRO at Art of Mentoring.
The deal involved Art of Mentoring's mentoring software platform and was initiated through a referral by a key partner, targeting a large athleisure retailer with a thousand participants across two programs.
Challenges:
Demonstrating the capabilities of a new platform while providing access to an outdated sandbox environment.
Managing complex use cases and ensuring the reassurance needed for a large-scale implementation.
Key learnings:
Delivering above and beyond service can differentiate and build trust with clients.
Warm introductions and strong partnerships significantly ease the go-to-market challenges.
Timestamps:
(03:48) Bijay's background leading sellers at big orgs and now international startups plus journey to Austin
(07:09) Beginning of the deal: initial contact and importance of the strategic 'thought leader' partner
(08:48) Challenges faced with the sandbox environment and platform transition
(10:28) Over-servicing to win the deal
(13:42) Importance of reassurance and client confidence
Resources:
Bijay Matthew on LinkedIn
Questions, comments, ideas - reach out to: [**https://www.linkedin.com/in/andrewkappel/**](https://www.linkedin.com/in/andrewkappel/)
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