At Gainsight, our purpose is to be living proof that you can win at business while being Human-First. That’s why Diversity, Equity, and Inclusion (DEI) remains a top priority going into 2025.
For Black History Month, we’d like to take the opportunity to shine a spotlight on some of our friends in the Customer Success (CS) space, who are making waves and establishing themselves as powerful leaders and change agents. Without further ado, here are four Black voices in CS who you should know.
1. Jasmine Reynolds, Enterprise Customer Success Manager at Appfire Flow
Jasmine Reynolds began her career in pharmaceutical and medical device sales, where she spent nearly a decade honing her skills in relationship management and strategic growth. Over the past 20 years, she has dedicated herself to the world of Customer Success and Customer Experience. Throughout her journey, Reynolds has prioritized building meaningful connections, driving value for her customers, and approaching every opportunity with intention. She takes pride in the path she has carved out for herself—one built on hard work, continuous learning, and an unwavering commitment to excellence. Reynolds advises, “The only person who will truly take your career seriously is you. What you invest in your career is exactly what you’ll get out of it.”
Currently, Reynolds serves as an Enterprise Customer Success Manager at Appfire Flow, where she leverages data-driven insights to help customers achieve their goals and unlock the full potential of their investments. Her work is fueled by a deep passion for superior customer experiences and creating scalable strategies that drive results.
“As a Black female professional, Black History Month holds profound significance for me,” says Reynolds. “It is a time to honor the legacy, resilience, and contributions of the African-American community, a legacy that has paved the way for professionals like me to thrive. This month is not just about reflection; it’s about celebration. It’s about recognizing the brilliance, strength, and innovation that our community brings to every field. I take immense pride in being part of this legacy and hope to inspire others to pursue their dreams unapologetically.”
Advice for Younger Professionals
When asked what advice she has for people still establishing their careers, Reynolds shared the following:
“Own your journey. Invest in your growth, seek out mentors, and never wait for opportunities to be handed to you. Be intentional, be bold, and remember that every challenge is a chance to build your strength. The business world will recognize your value when you do.”
2. Samuel J. Cummings III, CEO at Dataplant and Director of Education at Gen AI Works
Samuel J. Cummings III has built his career at the intersection of AI, Customer Success, and education. His journey took off as a data scientist at Gainsight, where he became fascinated by predictive modeling and its capacity to transform Customer Success strategies. Driven by a passion for making data actionable, Cummings advanced through the ranks in Customer Success, working diligently to bridge the gap between raw analytics and meaningful human experiences. From his early days at Gainsight to his achievements on LinkedIn’s Customer Success team—where he was honored with the Inspire Award—his mission has been to empower professionals with the tools and knowledge necessary to leverage AI effectively.
Currently, Cummings serves as the CEO of Dataplant and the Director of Education at Gen AI Works, focusing on democratizing AI education and enabling businesses to utilize data ethically and strategically. At Gen AI Works, he leads initiatives that help millions of professionals worldwide understand and apply AI in their industries, developing resources, courses, and strategic programs that enhance accessibility to this transformative technology.
Additionally, he is the Co-Founder of Dataplant, an Agentic AI platform that employs predictive analytics to aid businesses in proactively driving revenue through hyper-personalized customer interactions. The mission of Dataplant is to bridge the gap between data and human connection, ensuring that businesses can lead with empathy in an increasingly digital world.
“For me, Black History Month is a time of reflection and celebration—a reminder that triumph over adversity and dedication to innovation, leadership, and resilience are woven into the history of this country,” says Cummings. “I stand on the shoulders of pioneers like Katherine Johnson, Dr. Clarence ‘Skip’ Ellis, and countless others whose contributions to data science and AI often went unrecognized. As a Black professional in AI and Customer Success who has had to overcome my own odds to rise to leadership roles multiple times, I see it as my responsibility to never forget that my floor is the ceiling for those who come after me. Thus, in tech and beyond, those of us who have achieved any success must continue to rise further, while opening doors for others, ensuring that the next generation has the tools, mentorship, and opportunities they deserve.”
Advice for Younger Professionals
When asked what advice he has for younger professionals, Cummings shared the following:
“Don’t let others’ words define you. The best opportunities don’t come from waiting your turn—they come from showing up prepared, sharing your insights, and taking the initiative. In tech, and especially in AI, the landscape is constantly evolving. Stay curious, keep learning, and don’t be afraid to create your own table when fighting for a seat at one is proven futile.”
3. Mariah Bayne, Founder of Authentically You Coaching and Host of Growing the Middle
Mariah Bayne began her career in traditional insurance before making a bold transition into the tech industry, ultimately rising to the role of Director of Customer Success and Operations, where she led teams responsible for over $500 million in revenue. Hailing from a family with a strong tradition in law enforcement, stepping into the tech field was an entirely new path for her. Lacking a built-in network or industry connections, Bayne had to learn everything from the ground up. While there were numerous learning curves along the way, each experience helped shape her approach to growth and leadership. Having excelled in her career, she is now committed to passing on her knowledge to help others navigate their own transitions with confidence and clarity.
As the Founder of Authentically You Coaching and the host of the podcast Growing the Middle, Bayne shines a spotlight on individuals making an impact in roles that are essential to a company’s success, particularly during the often-overlooked middle stages of life and career. Through real stories and honest conversations, she aims to redefine what growth and success truly look like.
In addition, Bayne serves as the Senior Director of Placement at re:WORK TRAINING, where she collaborates with companies to source and place BDRs, SDRs, and CSMs into their organizations at no cost. In exchange, she asks that partner companies invest in candidates by mentoring, coaching, or leading workshops (with all materials provided) that equip them with the skills needed to succeed. This model not only provides companies with access to untapped talent, but also fosters a culture of giving back and professional development.
“I believe coaching shouldn’t start at the executive level—it should be accessible long before that,” says Bayne. “At Authentically You Coaching, I focus on affordable coaching services for professionals in the middle of their careers—those looking to grow, transition, or gain clarity on their next steps. Through skill articulation, goal alignment, and actionable career strategies, I help clients bridge the gap between where they are and where they want to be.”
Bayne continues, “By stepping out of my comfort zone and embracing the lessons of often being the ‘first’ and ‘only,’ I’m committed to reaching out and sharing what I’ve learned. My goal is to ensure that opportunities for others are endless—but more importantly, that their journey is supported. This is my commitment to honoring Black history every day—by creating pathways for others, fostering inclusive growth, and ensuring that our collective legacy shapes the future.”
Advice for Younger Professionals
When asked what advice she has for younger professionals, Bayne shared the following:
“Success isn’t about chasing titles or prestige. It’s about aligning your skills, values, and passions to create a career that truly fulfills you.”
She also shared, “I spent a lot of time learning to use my voice and understanding the power of leaning into my authenticity. The moment I stopped trying to fit in and started owning my unique strengths, everything changed.”
4. Davielle Shorter, Customer Marketing Manager at Gainsight
Davielle Shorter began her professional journey in high school, participating in the school’s Business Academy Program during her senior year, which featured a business-based curriculum and a half-day offsite business internship. This program jumpstarted her career by providing job experience even before she started college. Fast forward to 11 years later, she worked for the government at a scientific research laboratory as an Executive Assistant, while witnessing the rapid growth of Silicon Valley and the emergence of tech companies as a Bay Area native. After realizing that in her 20s she had attended more retirement parties than weddings, Shorter decided it was time for a change of environment. Intrigued by the perks and benefits of working in tech, she initially thought that she needed to be a computer scientist or programmer to land a job.
One day, she searched for “best places to work in tech” and came across a list of companies. While clicking through various websites, she stumbled upon Gainsight and was captivated by the intriguing job title of “Office Vibes Manager.” Recognizing that this was the opportunity she had been looking for, she applied and was brought in for an interview eight years ago.
As the Office Vibes Manager and Executive Assistant to the Chief Customer Officer at the time, Shorter worked in the Redwood City office—where nearly every Gainsight employee started their journey. She had the unique privilege of greeting every new Gainster on their first day, allowing her to form numerous meaningful connections over the years. Her initial role exposed her to many areas of the business and prompted her to explore how she could grow within the company and advance her tech career.
After four years, she transitioned to the Customer Success Operations team and eventually assumed her current position as Customer Marketing Manager, where she oversees the advocacy program. In this role, Shorter leverages both her operational knowledge and her passion for relationship-building, which she cultivated during her early days at Gainsight. Every step of her journey, from greeting new hires to amplifying customer voices, has been guided by a commitment to fostering genuine connections and driving meaningful change within the company.
Shorter says, “I learned about Black history from my family because schools didn’t really teach it. Realizing this made me see the bigger picture that there’s a lack of representation and inclusivity in so many areas of life. It’s what drove me to push for more Black voices and inclusion in tech, where it’s really needed and is why I am proud to be one of the founding members of the BIPOC TRG at Gainsight.”
Advice for Younger Professionals
When asked what advice she has for younger professionals, Shorter shared the following:
“What I would tell young professionals is that your identity is an asset, not a barrier. Embrace it, and let it guide you in creating pathways not just for your success, but for all who will follow.”
Gainsight’s Commitment to DEI
Given the evolving landscape, now seems like a good time to re-establish that at Gainsight, our commitment to Diversity, Equity, and Inclusion remains unwavering and intentional. DEI is something we’re committed to rooting in action rather than just words. We will continue to celebrate cultural events, support initiatives, and engage our Teammate Resource Groups (TRGs). Inclusion is, and will continue to be, fundamental to our mission and values—full stop.
Learn more about our BIPOC Teammate Resource Group and other TRGs here.
