Ask Ashley · 2026-05-22 · 25 min
Key moments - from our scoring
Substance score
46 / 100
Five dimensions, 20 points each
Jyl Feliciano brings two decades of experience building high-performing cultures at organizations ranging from Fortune 500 companies to startups, grounded in a personal evolution from masking her authentic self in financial services to becoming an advocate for inclusion and belonging. Her work at Highspot - a sales enablement tech company - centers on systems design rather than surface-level diversity metrics, using data to measure fairness across recruiting, onboarding, pay equity, development, and performance reviews. She addresses the current skepticism around diversity and inclusion work by depoliticizing language, focusing on workforce health data and the lived experiences of all employee groups (including working fathers and neurodivergent employees), and tying inclusive practices directly to business outcomes: retention, innovation, and revenue. Her approach - what she calls moving from "unconscious bias to unconscious inclusion" - removes emotion from equity conversations by embedding fairness into organizational systems from the start. Feliciano also emphasizes how generational differences shape workplace expectations: while Gen X valued steady paychecks, younger workers demand strong culture as table stakes, a shift her own children have helped her recognize and act on.
Instead of using DEI labels, Jyl focuses on the underlying work itself - running fairness audits on performance ratings, sharing workforce health metrics across all employee groups, and communicating business impact (retention, innovation, revenue) tied to equitable systems. She emphasizes that fairness and access are not political; they're operational systems that work for everyone.
Data is foundational: Jyl measures fairness at every stage of the employee lifecycle (recruiting, onboarding, pay, development, performance reviews), tracks how different employee groups experience the workplace, and connects equitable outcomes to business results. Without measurable success, she says, "success didn't happen."
Growing up around her grandparents' advocacy for housing, healthcare, and education equality taught Jyl about perseverance and policy change - her mother's lesson that "no" just means that person doesn't know, so keep going around, over, or under. This foundation drives her willingness to challenge systems and keep pushing for fairness even when progress is slow.
Jyl prioritizes faith and spiritual practice (reading her Bible, praying), strongly advocates for accessible therapy, builds relationships with thought partners doing similar work, and regularly reconnects with her "why" - a mission larger than work itself. This helps her focus on what she can actually move rather than outcomes beyond her control.
Be bold and courageous; don't be afraid to fail or ask for what you need. Jyl's own example: she emailed retired Fortune 500 CEOs on LinkedIn and secured mentoring relationships simply by asking. She'd tell her younger self that things work out and every experience, even scary ones, contains a lesson.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains scattered substantive points about systems-driven inclusion, measurement frameworks, and messaging strategy, but these are diluted by considerable filler, repetition, and motivational platitudes. For example, Jyl's framework on 'moving from unconscious bias to unconscious inclusion' and the insight about architectural system design (recruiting to performance reviews) are concrete, but they are surrounded by non-specific advice like 'courage is needed' and generic self-care commentary. Most B2B operators would extract 2-3 actionable ideas rather than a dense concentration.
if you construct systems that drive behavior you don't necessarily have to call out the component of the system that's built to do what
if you can't measure success then success didn't happen at least from a workplace perspective
The core framework - systems design for equity, measurement, and narrative management - is sensible but not novel in HR and DEI circles. The reframing of 'diversity language' to avoid loaded terminology is somewhat contextual and practical, but the broader thinking recycles familiar concepts (mentorship matters, authenticity drives innovation, culture ties to revenue). The episode lacks contrarian insight or first-principles challenge to dominant DEI orthodoxy; instead it offers a softer repositioning within it.
systems development around inclusive work environment has always been the answer to solving some of these equity gaps
we've had to take a step back and actually just talk about the thing versus putting a label on the thing
Jyl Feliciano is a Global VP of People, Culture & Belonging at a legitimate SaaS company (Highspot) with 20 years of hands-on experience in building culture and inclusion across Fortune 500 and startup contexts. She is a practitioner, not a consultant-only voice, and has concrete operating experience. However, the episode is not an in-depth operational deep-dive; it reads more as a personal narrative, which limits extraction of systematic insight. She qualifies as credible but not exceptional caliber for a substantive B2B podcast.
I currently serve as the Global Vice President of People Culture and belonging for Highspot
I've had 20 years of experience um helping guide and coach executives and leaders from Fortune 500 down to kind of smaller start UPS on building high performing cultures
The episode is sparse in concrete data, named examples, and quantified outcomes. Jyl mentions Highspot and briefly references a mentor (Paige Scott) and a LinkedIn outreach to retired airline CEOs, but provides no metrics on retention impact, revenue lift, or specific case studies. Claims about fairness, innovation, and retention are asserted without supporting numbers or measurable benchmarks. The lack of specificity severely limits actionable learning for operators seeking replicable frameworks.
so we've been very intentional about how we market and how we tell the employees story through data and the lived experiences of employees
our commitment to employees around fairness and access are being upheld
Ashley asks warm, open-ended questions that allow Jyl to tell her story, but rarely pushes back, challenges claims, or digs deeper into specifics. Follow-ups are mostly affirmations ('I love that') rather than probing questions. For instance, when Jyl discusses navigating DEI skepticism, Ashley doesn't ask for concrete examples of pushback or metrics on employee perception. The conversation feels supportive and friendly but lacks the intellectual rigor and productive disagreement that would extract richer insight. Questions are good-intentioned but soft.
I love that finding yourself by being yourself I'm curious were there any significant turning points challenges along the way
I love that I love that shift right there that's good that's good
Computed from the transcript - who did the talking, and the words that came up most.
In this enlightening episode of Ask Ashley, host Ashley Russo welcomes Jyl Feliciano, the Global Vice President of People, Culture, and Belonging at Highspot. With over 20 years of experience, Jyl shares her inspiring journey from the financial services sector to becoming a leader in culture and belonging. She reflects on the challenges she faced, including impostor syndrome and the pressure of conforming in a male-dominated industry, and how these experiences shaped her mission to create workplaces where authenticity thrives. Jyl emphasizes the importance of courage in leadership and the necessity of data-driven decision-making within DEIB initiatives. She also discusses the role of mentorship in her career and how her upbringing as the granddaughter of civil rights activists influenced her passion for advocacy. Throughout the conversation, Jyl encourages leaders to prioritize human connection while navigating the complexities of modern workplace dynamics. This episode is a powerful reminder that fostering an inclusive culture is not just a trend but a vital component of organizational success.
Transcribed and scored by The B2B Podcast Index.
welcome to ask Ashley the podcast where we shine a light on the unsung heroes of the workplace I'm your host Ashley Russo financial AI board member thought leader and wealth management advisor each week we sit down with inspiring leaders exploring their journeys motivations and the real challenges they face from job insecurity to the evolving role of AI in a world where many feel overlooked these guests are building hope and connection for their colleagues join us as we uncover their stories and discover how they're making a difference one conversation at a time hi everyone Ashley Russo here with one of my favorite humans on the planet we have become BFFs forever for life will you please introduce yourself to everyone absolutely well hello everyone I am Jyl Feliciano I currently serve as the Global Vice President of People Culture and belonging for Highspot which is a tech sales company think sales enablement train coach sales to get in close deals faster so really excited to be here overall I've had 20 years of experience um helping guide and coach executives and leaders from Fortune 500 down to kind of smaller start UPS on building high performing cultures that thrive on the center of inclusion belonging and the human uh the humans that make those organizations actually run so I'm excited it's an exciting time to really talk about this topic but then also other things about leadership and finances so Ashley thank you for inviting me I'm excited to get into it yes so many things so many things to talk through let's start with can you walk us through your career journey and what initially inspired you to focus on inclusion equity diversity and belonging yeah absolutely so I started my career um in financial services actually um and starting right out of college um you know I had to really learn how to show up like me uh in the workplace and what that means is um it was majority you know male dominated um there weren't a lot of you know women in leadership uh women of color I'm also neurodivergent I'm a parent like I was all these other isms and to find my voice was a struggle Ashley and to be open and real I you know Learned to assimilate so I Learned how to play golf uh I was actually really good at it but it was really expensive and I didn't enjoy it but I Learned you know to watch different movies in terms of understanding kind of the cultural references around me um and I just was exhausted masking and I was sitting in a conference room by myself and I thought you know what I'm done I'm done being whoever I'm portraying myself to be I want to be authentic to who I am how I grew up the point of view I bring to the table cause guess what I am a customer right um and I can actually advocate for folks who look like me and have lived experiences and that is what challenged me to uh go into diversity equity inclusion belonging any acronym that folks are using these days because I Learned that if you actually create an environment that allows authenticity to enter you have the grounds for high um retention and innovation is at its all time high and there is a revenue um component to this so ever since then I am gonna be the stand out I want to continue to advocate for others and because I don't fit in it may be a great candidate to lead and diversity equity inclusion and belonging fascinating fascinating I love that finding yourself by being yourself I'm curious were there any significant turning points challenges along the way that sheet how you approach your work that's a really great um question I would say a couple um the first is you know I suffered from imposter syndrome a lot earlier in my career especially as I started to get into the leadership ranks um and what a what that did was it actually silenced my voice in a lot of business decisions and a lot of my ability to build relationships in an effective way and actually I had to work through that I had to really lean on mentors I had to do some inner self work to say you know what I belong I belong um and once I Learned to carve space out for me to have discussions but also to influence without authority that for me was a turning point as to how I can actually show up lead and then set an example for others around me to do the same um the other is just mentorship right I had a mentor her name is Paige Scott um and funny thing Paige though was my boss and a later mentor in my early career she now is a customer of ours I see her at conferences um and she would carve out spaces for me to you know present at the executive level go to board meetings um spaces on all company all hands um so that did help me understand that access was one of the key formulas for success of all employees so I think those were some of the turning points working through impostor syndrome and then being lucky enough to have one of the best mentors that believed in me and made space even though I didn't think I was ready for it wow that's a really good message that you didn't just show up at this level you worked to get your um and allowed support in right that's that's sometimes the hardest part I'm curious did your upbringing your childhood did that shape the way you view things or have an impact on your experience and journey yeah absolutely so um I am a uh Chicagoan through and through born and raised but I'm also the granddaughter of civil rights activists and Chicago so I was the kid outside of the town halls like eating my chips and my Barbie dolls and but what I Learned is that advocating and pushing um policy that change and shapes the trajectory of one's lives is one of the most important things that we can do and I'm not trying to do a political rant here but it truly was a part of building the core of who I am as a person as a leader um I also Learned about perseverance I've seen so many times where um you know my parents my grandparents really advocated for different things Equality for housing and healthcare fair educational you know um resources and they weren't successful the first time but they kept going they kept going and I remember my mom told me when someone tells you no it's not a no it's just that that person doesn't know so keep going go around them go over them go under them keep going and those are some you know early on lessons that I Learned that really you know suit me to today I'm not afraid to fail I'll keep going I'll go up around down we'll get there one way or the other oh I love that I love that so let me ask you this question how do you balance making data driven decisions and bringing that to the human side of of diversity and inclusion initiatives especially in this changing societal conversation around diversity and inclusion yeah you know one of the things that I am grateful for um Ashley and you know I've been doing this work for over 20 years but I started out as an operational engineer and what that taught me is if you construct systems that drive behavior you don't necessarily have to call out the component of the system that's built to do what okay so systems development around inclusive work environment has always been the answer to solving some of these equity gaps and lack of belonging and engagement so far um so I Learned how to build the second thing is I Learned that if you can't measure success then success didn't happen at least from a workplace perspective right so not only did I have to learn how to layer in a through line of inclusion belonging and fairness into the employee experience everything from recruiting to onboarding pay equity how one gets developed to you know how one's performance review um is facilitated in a fair manner way it's about how you architect it from beginning to end okay to having data to not only understand how each of the employee phases perform under those guidelines of fairness and access to all people the thirdly and you'll enjoy this Ashley it's about marketing and communication because we have to really talk about what this work means to us internally as opposed to leaving it up to kind of external forces to mold the narrative so we've been very intentional about how we market and how we tell the employees story through data and the lived experiences of employees and how that through line has driven business impact innovation enhanced our AI strategy um helped us retain top talent and then how that ties to our revenue so it isn't a machine it's an engine and it should just naturally be something that a company does I call it moving from a state of unconscious bias to unconscious inclusion oh I love that I love that shift right there that's good that's good so it sounds like because there's a system in a process and data in place it also can lead to removing the emotion and the emotional reaction and making it more of a process I'm curious how you're dealing with the balance um with the the skepticism that is out there uh right now in this moment in time towards diversity and inclusion how that impacts company culture how that impacts you as a human and posing this is in in this process and if the system in process helps you just simply get out of that you know skepticism that's out there yeah I I love the conversation Ashley like let's do it let's face it head on but you know a few things so one I am extremely lucky and privileged to have an amazing leadership team that knew that this work was critical to driving business outcome this was never about um getting points you know with um you know kind of the external you know layers around like our brand and our image it was simply the right thing to do right so our why was really really different than maybe some others right where their why was tied into hey this diversity thing is like actually profitable right now like let's invest and do all those things right so the intention um behind it so um they very much are still committed to the journey but we do recognize that we serve customers we recognize that the world around us um some in the world around us may feel different about this topic so one thing that has changed is the language towards it right and honestly I don't really think that we there was a unified understanding of what diversity equity inclusion really was I think it was up to interpretation based upon the lens in which you see the world and that was problematic so yeah so what that means is um we've had to take a step back and actually just talk about the thing versus putting a label on the thing right so the fact that you know I'm saying hey we're just running an analysis to make sure that you know the performance ratings um you know our fair equitable and you know right size for kind of what we expect across the different performance categories for our distribution we're just doing a check to make sure that we're you know aligned with market standards um so that our commitment to employees around fairness and access are being upheld no issues there okay um if I you know share data on our workforce right just a workforce health data it's not let's look at these diversity metrics because diversity means different so it's just metrics right so let's look at the workforce metrics and be able to tell the story of every employee group and intersection of employees because working dads I really appreciate when I talk about them and the role that they play in the family of parenting right now um so we just open it and just say how are people doing and then we then we look at the different pockets of people and how they're experiencing the workforce and being okay with what that is and you know working to bring awareness but support across all employee bases so that is how we're really navigating through this time but we are lucky because our commitment and our why hasn't you know hasn't changed you mentioned dads and it brings me to the thought of parents right so I feel like kids I know you're a parent I'm a parent obviously it it can influence how we see the world because obviously we're very aware that there'll be a generation that inherits the world that we leave yeah I'm curious how being a parent raising children how it's influenced your viewpoint as a leader yes um well first of all you can't see the back of my hair because I think I have plugs that are pulled out because raising children is no easy um feat but I will say that No.
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