James Gilbert 🙏🏻

Bloomerang

Empowering fundraisers and nonprofits to do what they love and build a world inspired by giving

Vice President Demand Generation

noble

Advisor

CloudSpot

Strategic Advisor

Sendoso

CMO Collaborative

SLC CMO Collaborative Chapter Leader

Flip (formerly RedRoute)

Recruited to bring extreme growth. Structured foundational growth engines. Historical pipeline, MRR, ARR, and retention. Built a team from scratch. Structured a rename, rebrand, and new website within 4 months. Built and ran our podcast, outbound engine, and all growth engines. Led Flip to Pavillion’s category king finalist in 2023. Grew MRR and pipe 12% MoM, 92% retention rate.

Chief Marketing Officer

BUSINESSNEXT

•	Grew from Series A to Series C 
•	Built a demand gen engine which led to a 10x growth in ARR
•	Held a steady CAC ratio of 3:1
•	Decreased sales cycles from 12 to 4 months
•	Developed and led culture
•	Developed our US GTM strategy through partnerships and community.

CRMNEXT

GM North America & CMO

California State University, Long Beach

A focus around Big data. I served as a representation of big data and how it can be leveraged across business units.

Big Data Board Of Advisors

Cisco

- Helped develop a global demand gen process and ABM across multiple products
- Discovered $25M in annual savings from overlapping technology and built a consolidation plan for a single tech stack to be used.
- Continued to lead marketing for CloudCherry post-acquisition
- Helped lead strategy and GTM for the collaboration BU with ABM for APAC, EMEA, North America, and South America. This yielded net new market share, cross-selling opportunities into other BUs, and massive pipe and a 1,110% increase in revenue.

Director RevOps and Insights

Passionate about bringing humanity to business. 

High growth leader, Built teams from scratch from 0-120, 3X CMO with a background in RevOps, Demand Gen, and RevOps. 2 Successful exits. I’m a bit of a data freak but I am super creative and have come up with some insanely fun and engaging campaigns. Enterprise leadership roles at Cisco, Verizon, and AGCO, instrumental in driving massive growth. Strengths are driving a growth engine that can scale while building a solid team that can operate and have fun. $0-$150M and Seed - Series D is what I have done several times now.

The personal side of me: I am a father of 4 with an amazing wife, this is what drives me. I am a sports enthusiast & Utah Jazz fan #takenote. 

I believe the biggest gap in today's world is our lack of being human even when there are differences. Be kind in all that you do, it always pays off.

Today our 19yr old son flies to Madagascar for 2 yrs.

He won’t set foot in the US again for 2 yrs.

Sleeping with a mosquito net every night and doing the Lord’s work.

Seeing his growth in 5 weeks it’s crazy. 

He has already turned into such a great man.

Seeing him learn Malagasy at a basic level, and to be able to say full sentences in 5 weeks is even more remarkable.

We are proud of him. But wow is it hard. 

“Mom and dad I know you guys love me, but I got this. I am ready to be on my own serving those around me.” Those are words that hit us hard last night as we spoke to him.

We don’t know the adventures he will have but we know they will be incredible!

3x CMO | Father of 4 | AI-Driven GTM Strategy | Scaling Startups to Market Leaders

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There’s a part of my story I don’t talk about much anymore.

Not because it’s painful.
But because life got busy.
Work got louder.
And somewhere along the way, the thing that shaped me the most got pushed to the background.

Most people today on here know me as a dad of 4, a previous multi CMO, and a GTM leader.

But long before any of that…
I struggled to share the most important aspect of who I am.

For fear of losing a job or not being able to get the next one, For fear of judgment, you name it and I let it get in the way.

You don’t get to choose what happens to you, but you always get to choose who you become because of it.

At a young age I lost my eyesight. Yes you read that right. 

I sat on transplant lists for 4 years (miracles I will later share here)

It happened faster than I would have hoped.
It broke dreams and things I wanted. 
But… bridged new opportunities.
I don’t, and won’t ever give up!

One day I woke up and realized my world was blurring, literally and metaphorically.

I didn’t know what life would look like.
I didn’t know if I’d ever have a career.
I just knew everything was about to change.

And it did.

Losing my eyesight forced me to learn how to see differently.
To work harder than anyone else.
To think differently.
To listen differently.
To create differently.

It’s the reason I taught myself piano by ear.
It’s the reason I think the way I do.
It’s why I am so creative.
It’s why I care so much about the disability community and giving back.
It’s the reason I see patterns in data, stories, and people that most overlook.

I’m going to start sharing more of that journey again, because it’s shaped every part of who I am as a leader, a builder, a father, and a human.

And because if my story helps even one person who’s in a dark place right now…it’s worth telling.

Losing my eyesight didn’t give me a choice.
But choosing how to respond to it did.

And that’s the part I want to share more of because someone out there is facing their own version of “this wasn’t supposed to happen.”

If that’s you, hear me out:

You may not control the setback.
But you absolutely control the story that comes after it.

A dinner this last week turned into a moment I didn’t see coming.

I was catching up with some old friends at Breakthrough. We went to a dinner invite with a BI vendor we’re exploring when I found myself sitting next to Jerry Henry. Who was one of the first people who ever personalized outreach to me. Back in 2013 or 2014, he reached out about the Utah Jazz, and it stood out because it felt… genuinely human.

Still to this day he is one of a handful who did it right in 20 yrs.

We laughed about that, but then the conversation turned deeper.

Jerry brought up the very first video series I ever shared. It was my story about losing my eyesight, learning piano by ear, and discovering creativity and data as two sides of the same coin. I never knew how closely he followed it.

This was way before video became such a big thing (should’ve stuck to that).

Then as others heard about the vague video series people asked to hear it as well.

And it reminded me of something:

Our stories matter. Not because they’re perfect, but because they’re real.

As soon as I finished, someone shared their mom was struggling with her eyesight even had one of the diseases I had. That opened a conversation about accessibility, the disability community, and how often their needs are overlooked in business.

It sparked Justin Cook telling me I should start a nonprofit, not a bad idea actually. 

All from one story.

Sometimes inspiration doesn’t shout.
Sometimes it shows up quietly, in moments you never expected.

My mom inspired me to make that video series back then, but every time I retell the story to others, it inspires me to keep doing it.

The amount of fake AI profiles on this platform is growing at a crazy rate.

In my scroll today I noticed a weird pattern. So, I dug a bit deeper.

This sparked me double-checking all the other posts I found valuable.

I went through a dozen posts from what I thought were people. 

All with a promise, comment x and I’ll send it. Interesting that all the fake ones used this same format.

7 out of 12 were AI and not humans.

I’m curious who else is seeing this stuff. 🤔

Rob Dwyer

Happitu

Launched AI-driven conversational analytic platform, enhancing agent engagement and operational efficiency.  
Identified and developed strategic partnerships.
Cultivated existing partnerships generating product-led growth and additional product adoption.

VP - Customer Engagement

Launched a new SaaS product leading the GTM strategy and execution.
Conducted product demonstrations and successfully onboarded new partners.

Director of Customer Engagement

Customer Direct

Successfully launched multiple new programs while leading the migration of virtual training platform.
Implemented new streamlined Sup/Agent onboarding process via SharePoint automation.
Selected as Featured Contributor for ICMI.

While still overseeing Training and Quality, also oversaw all marketing and sales functions.
Responsible for developing and delivering all client proposals and contracts.
Streamlined and documented backend processes related to hiring, onboarding, and training.

Designed, Implemented, and Trained all staff on Supervisor Coaching Model to drive performance and culture.
Worked directly with partners and internal operations team, facilitating quality calibrations and identifying/closing agent skill gaps.
Served as operations stakeholder for new SaaS product development and pre-launch GTM strategy.
Developed a variety of custom reports from QA performance to internal training VoC reporting.

Director - Staff Development

Successfully built a training department including staff, systems, processes, and curriculum.
Implemented Learning Management System and Virtual Training Platform, increasing New Hire trainee capacity from 12 agents to 30+ agents, allowing both rapid ramp capabilities for new clients and eliminating recruiting restrictions to the greater St. Louis area resulting in hiring expansion to markets in Kansas, Arkansas, Kentucky, Tennessee, and mid-Missouri.
Provided direct oversight, coaching, and development of Training team and Quality Assurance team.

Manager of Quality and Learning Development 

Convergys

Served as Global leadership and coaching consultant directly supporting 11 lines of business over 6 sites in the Western Hemisphere.  
Served as Global Leadership Training SME, Master Trainer, and Coordinator for 23 sites.  
Led initiative to virtualize two-week leadership training workshop to support the global enterprise.

Leadership Coach & Corporate Trainer

Developed Curriculum for New Hire Training.
Acted as SME for Virtualization Effort of existing training material.
Served as mentor to new trainers in the department.
Achieved over 100% to goal for all four Key Performance Indicators for 2011

Associate Trainer

Led both classroom and virtual training for New Hires and continuing education.
Achieved highest score ever for Arnold Site Trainer during client Trainer Certification (July 2011).

Program Ready Trainer

Averaged over 100% to goal for all Key Performance Indicators for 2010 as retention agent for US wireless telecom provider.

Tele-Commute Agent

VP - Customer Engagement at Happitu 🔹 Podcaster 🔹 Coach 🔹 Facilitator of Learning 🔹 Wielder of Curiosity

As a seasoned VP of customer engagement, I specialize in empowering small and medium businesses with AI-driven conversational analytics and outsourced contact center solutions. With over a decade of experience in customer experience (CX) and customer success, I bring a deep understanding of how to unlock valuable customer insights and drive engagement.

My expertise lies in:

- Customer Success Management: Leading initiatives to enhance customer satisfaction, loyalty, and retention.
- AI & Machine Learning: Implementing cutting-edge AI solutions to streamline customer interactions and gather actionable insights.
- Conversational Analytics: Leveraging advanced analytics to understand and optimize customer journeys.
- Contact Center Operations: Enhancing the efficiency and effectiveness of call center teams through innovative strategies and technology.
- Customer Support Excellence: Building robust support systems that ensure a seamless and positive customer experience.
- Training & Leadership Development: Mentoring and developing high-performing teams to deliver exceptional customer service.

In addition to my roles at Happitu and Customer Direct, I host the "Next in Queue" podcast, where I interview global experts in Customer Experience, Contact Center Management, Customer Support, Customer Success, Training, Leadership, and Technology. Each episode provides valuable lessons and insights from industry leaders, from CEOs to frontline staff.

Connect with me to explore how we can drive customer success and engagement in your organization. Follow my #StarWarsLessons series for unique business insights inspired by Star Wars characters.

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