Career Coaching

Diana's work experience includes serving as an in-house coach to early career employees, high potentials, and new people managers at the National Basketball Association, as well as leading talent development and culture-building at a national nonprofit. An experienced recruiter and interviewing skills coach, her professional journey started as a university career counselor. She is certified as an Associate Diversity Coach, Hogan and MBTI practitioner, and trains on the human experience of change in organizations. She received her BS in Communications and MA in Higher Education from New York University.

Welcome! I’m a certified life coach (Erickson Coaching International, ICF-accredited) with 10+ years leading People Operations at companies like Grammarly, CZI, Confluent, and Dropbox. I specialize in career and relationship coaching—because I believe that a better life begins with better relationships, and at the heart of everything we do—whether at work or home—is connection. Coaching has been transformative in my own life, and I’m passionate about creating that same space of clarity and growth for others. There’s no greater joy than helping someone move forward with purpose and confidence. My style is empathetic, intuitive, and rooted in asking thoughtful, perspective-shifting questions that help you rediscover your strength and direction. I’ve supported over 60 professionals across industries and life stages. Education: BBA from Simon Fraser University; executive programs at Stanford GSB and UC Berkeley Haas. If you’re navigating a transition, craving more alignment, or feeling stuck—let’s connect and chart your next chapter, together.

Over the past eight years, I’ve coached more than 60 professionals through high-stakes career transitions across law, finance, and private equity. My own path, from a top-10% graduate of Howard University School of Law to M&A attorney at Paul, Weiss and Kirkland & Ellis, and now a middle-market private equity fund while earning my MBA at Wharton, gives me a unique perspective on navigating elite recruiting and ambitious pivots. I specialize in helping clients clarify career goals, tell a compelling story, and secure offers in competitive industries. From resume and LinkedIn optimization to networking strategy, interview prep, and offer negotiation, my coaching blends insider knowledge of Big Law and high finance with a structured, data-driven approach. Whether you’re seeking your first post-graduate role, planning a major industry switch, or aiming for leadership positions, I provide actionable guidance and proven tactics to help you achieve the next stage of your career.

I have coached and mentored students and early-career professionals across universities such as GBSB Global Business School, ESADE and MSMK University, mainly supporting candidates with under five years of experience. My work has focused on helping students clarify their career direction, improve their CVs and LinkedIn profiles, prepare for interviews, and build a stronger narrative around their experience, skills and goals. Alongside my coaching work, I bring 15+ years of international experience across marketing, business development, startups, SaaS, AI, healthtech, consumer goods and education. This allows me to help candidates connect their academic background with real market opportunities and make more confident career decisions.

With over 15 years of enterprise SaaS experience across companies like Salesforce, Red Hat, ServiceNow, Symantec, and NetApp, I've lived every stage of the Customer Success career path — from individual contributor to Senior Manager leading high-performing teams across the LATAM market. I know what it takes to break into CS, level up into leadership, and build a career that travels across organizations and geographies. I'm bilingual (English/Spanish) and specialize in helping mid-career professionals and LATAM-based talent navigate the nuances of the US enterprise SaaS job market — from resume positioning and ATS optimization to LinkedIn presence and executive storytelling. I've guided dozens of CS professionals through pivotal career moments: landing their first CSM role, transitioning into management, repositioning after a layoff, or targeting Director and VP-level opportunities at global tech companies. My coaching is practical, structured, and grounded in what actually works in real organizations—not theory. If you're ready to stop guessing and start moving, I'd love to work with you.

With a diverse background spanning medicine, consulting, and strategic operations, I bring a unique perspective to career development coaching. I trained as a physician at Yale, worked at BCG, and later led strategy and innovation work at the Gates Foundation and Illumina. My own career has involved several complex pivots. I’m particularly good at helping people navigate high-stakes career transitions, whether that means deciding between several reasonable paths, repositioning their experience, or preparing for an important interview. I tend to take a data-driven approach to career decisions, while recognizing that the best choice is rarely purely rational. A good career move has to make sense on paper and also work for the life you actually want.

Finding a job is a function of identifying what sits at the intersection of your skills, talents, and interests. If you're going to work for the rest of your life, why do something that you hate? There are systems you can use to figure it out much quicker than peers. I call it the Career Hypothesis method. If you truly act from a place of genuine curiosity and are moving in alignment with what you want, then I'm confident you can get any job you want.