James Gilbert 🙏🏻

I am the current VP of Demand Generation at Bloomerang with a background as a 3X CMO. I have with a proven track record of helping companies scale from early stage through late growth, building marketing functions that drive sustainable scale. I thrive at the intersection of brand, demand generation, and AI-driven go-to-market strategy, translating innovation into market momentum.

Start-up stages: Seed to Series D & $1M - $150M
Enterprise experience at Cisco, Verizon, and AGCO

Core expertise includes:
- Building and scaling global marketing and growth organizations
- Harnessing AI as a growth engine, with hands-on experience in agentic AI models, Voice AI, and leading platforms such as Claude, ChatGPT, Gemini, Perplexity, and more to transform marketing, customer experience, and operational efficiency
- Partnering with CEOs, boards, and investors to guide companies through critical growth inflection points
- Positioning organizations for long-term success through strategic storytelling, brand building, and market leadership

In addition to my executive roles, I serve as an advisor to founders and leadership teams, an investor, and an author on the future marketing, AI and modern go-to-market strategy. These roles keep me deeply connected to emerging technologies and the evolving growth landscape, enriching the perspective I bring to every company I help scale.

I bring a balance of strategic vision and operational rigor, ensuring marketing not only shapes the narrative but also drives measurable business impact in revenue not just pipeline. Today, I am focused on helping organizations harness AI and modern growth strategies to reach their next stage of expansion with clarity, momentum, and scale.

Vice President Demand Generation

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

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.

taplio

The Battle

James Gilbert 🙏🏻

Rob Dwyer

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