Diana Olympia

AI Strategist & Educator | Former CS Executive

Los Angeles, United States (-08:00 UTC) Englishfrom Los Angeles, United States
Usually responds in 1 day
Free
Price per hour
30 min
Time Blocks Available
5.00
8 reviews / 12 sessions
Thu
29
Next availability

Bio

I help small businesses and scaling teams cut operational friction using AI and automation. I have leverage my 17 years of GTM, strategy, and operational experience to make sure these systems actually work and actually scale as you grow. I've introduced hundreds of professionals to practical AI implementation through workshops and 1:1 coaching, with a focus on helping solo operators and small teams automate the work that's eating their time. My approach: start with what's broken, build the simplest system that fixes it, and only add AI where it earns its place. On the CS side, I led Foursquare's customer success function to 5-year retention highs managing enterprise accounts including Meta, Walmart, and American Express. In addition to B2B SaaS, my experience spans traditional media (Viacom), ad tech (Inscape), and content partnerships (Hulu). Most impactful for: * Small business owners automating operations for the first time * Teams that want to implement AI tools that actually get used * Founders building CS systems without full-time hires * Enterprise onboarding, churn prevention, and expansion strategy Specific expertise: AI workflow design, automation platforms (Zapier, Make, n8n), health scoring systems, QBR frameworks, churn prevention playbooks, expansion identification, enterprise onboarding. What I love about mentoring is helping founders skip the costly trial-and-error phase and implement frameworks that actually work. As a woman of color who's navigated leadership across corporate and startup environments, I especially enjoy working with founders who value diverse perspectives.

Expertise


  • Artificial intelligence

    Founder of AI Made Simpler. I run practical AI workshops for professionals and train small teams/SMBs to put AI to work. I write a newsletter on real AI implementations that solve real problems. Client builds include a customized QC system for content production and agentic workflows for performance tracking. Hands-on with Claude Code, Zapier, Make, n8n, and most vibe coding tools. Built a SaaS app (Node.js/PostgreSQL/React) đź“© https://aimadesimpler.beehiiv.com/

  • Customer success

    Front-line manager running a team of CSMs, also risen through ranks as an IC from associate CSM all the way up to Principal CSM. Expertise managing B2B SaaS Tier 1 enterprise clients - retaining, expanding, and ensuring it's a strategic not just transactional partnership.

Toolkit


  • Salesforce logo

    Salesforce

    I can share best practices for creating and monitoring Red Accounts and Health Scores, training your teams to identify MEDDPICC for each key account, how to track renewal forecasting, onboarding milestones, and more

Experience

  • Moms First

    Associate Producer

    From post-war propaganda to culture wars pitting “girl bosses” vs “trad wives,” this upcoming documentary reveals forces that have defined American motherhood and opportunities to come together across political division. The film is produced by Emmy-nominated Culture House Media in partnership with French Tuck Media, the production company founded by Queer Eye star Tan France, and Moms First, the national non-profit organization using media to educate and mobilize millions of moms.

  • Eleuth

    Founder

    Consulting and advisory services for early stage startups and scaling organizations. AI Strategy & Enablement • GTM Strategy • Customer Success 0 → 1

  • AI Made Simpler

    Founder

    Practical AI workflow design and implementation for small businesses, founders, and solo operators. https://www.aimadesimpler.co/

  • Foursquare

    Manager, Customer Success

    As head of Foursquare's Enterprise Customer Success team: * Coached BU to 90% NRR (5-yr high), managing team of 4 CSMs * Implemented training and development programs to enhance CSM skillsets: technical support excellence, product education, account strategy, renewal activities, and discovery As Principal Account Manager: * Drove high levels of positive customer experience and satisfaction: 89% NRR and 94% logo retention, on average, during IC tenure with several 100% quarters on $12M book of business * Selected for inaugural FSQ Emerging Leader program: < 2% acceptance rate across global workforce; nominated by manager and sponsored by CRO

  • Inscape Data, Inc.

    Director, Customer Success

    Managed Tier 1 and 2 Enterprise partnerships with major TV networks, MVPD affiliates, ad tech platforms, and other key customers * $18M book of business under management ($2M ACV on average) * Systems architect of 15+ enhancements to internal workflows and processes that streamlined operations and resulted in net positive impact to customers * Helped build out growing CS team: involved with hiring, led training and onboarding for new staff * Partner roster highlights: Comcast FreeWheel, NBCUniversal, MiQ

  • Viacom

    Director, Strategy and Business Operations

    Contributed to $4B+ in affiliate revenue across MVPD and vMVPD deals, advising on strategic TVE and New Media rights, helping secure successful carriage renewal agreements with Comcast, DISH, DirecTV among other major providers Generated strategic recommendations that guided distribution initiatives for Viacom media network portfolio * Produced dozens of decks and insights for senior executives, C-Suite, and Board of Directors on key strategy questions facing VMN and overall media industry * Sample topics: TV Everywhere, content windowing, international strategy, new business models, partnerships Managed development and technical end-to-end execution (10+ implementations) of new media products across all key affiliate partners, guiding from inception to launch * Key project highlights: TV Everywhere, Dynamic Ad Insertion, Home Based Authentication, Video On Demand

  • NewsCred

    Business Development

    Developed, managed and executed sales enablement programs for all 8 strategic channel partners and internal NewsCred sales org to support launch and growth of partnership ecosystem * Partner roster highlights: LinkedIn, Outbrain, Spredfast, Nativo, King Content

  • Hulu

    Customer Success Manager - Content Partnerships

    Primary post-sales owner of licensing partnerships; responsible for day-to-day management, QBRs, growth, and renewals; promoted within 10 months of start date * $100M+ in revenue under management, across 90 content partnerships; Content Lead across key Tier 1 content owners and emerging growth verticals: - Major networks: NBC Universal, CBS, Scripps - Kids (Sesame Workshop, PBS Kids, Saban) - Korean/Asian content (DramaFever, Viki, SBS, KBS, MBC, CJ Entertainment) Oversaw launch of major content deals and new partnerships (E!, Bravo, NBC, CBS) * 4,000+ new hours of TV and film programming added to the service under stringent timelines Drove 3x revenue for Korean Drama vertical during tenure * Led more closely integrated partnership efforts across operations, content curation, and internally championed significant efforts to increase promotion across marketing, PR, distribution, and editorial to capitalize on this underserved audience Developed and implemented new operational processes and workflows that streamlined large content library launches * 10,000+ assets total impact Additional leadership role: * Founding member of Hulu GiveBack Advisory Board, Hulu's internal philanthropy board

  • A+E Networks

    Integrated Ad Sales Planner

    Prepared on-air media proposals and developed promotional concepts for national advertisers, resulting in ad revenue for History network of brands * $95M in revenue under management; contributed to $4.5M in new business Managed custom integrated campaigns for high-profile clients * Sample roster: Walt Disney Studios, The Weinstein Company, Acura, Priceline.com, Best Western, POM Wonderful, Honda Motorcycles, Behr Conducted strategic analysis for pricing and revenue optimization decisions Administered West Coast sales office operating budget Supervised and trained sales assistants and interns

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