Jess Osborn

About Jess Osborn

Passionate About People, Performance and Disruptive Technology.I believe that when people and businesses are empowered to be their best, incredible things happen. As a global Customer Success leader, I bring a human-first approach and a results-driven mindset, helping teams thrive, businesses scale and customers successfully adapt to emerging technologies. I’ve led high-growth teams across international markets, driving revenue impact and helping organizations navigate disruption from martech and fintech SaaS to AI. My expertise lies in building and scaling Customer Success organizations that drive retention, expansion and revenue growth.What I’ve Learned & Achieved: • Customer Feedback Fuels Innovation: The best companies evolve with their customers. I have spent my career turning customer insights into product strategy driving market fit and adoption. • Customer Success is a Business Driver: I’ve transformed CS from a cost center into a revenue-generating function by designing services that directly solve customer challenges and provide the support they need. • Disruptive Tech Must Solve Real Problems: Technology alone isn’t enough. Success depends on solving the right problems with the right approach. Solutions must adapt to regional differences in infrastructure, regulations and customer behavior. • Scaling Requires the Right GTM Motion: Self-serve businesses can unlock exponential growth by adding a sales-led motion and transitioning to committed contracts, but only with accurate forecasting and accountability to prevent overselling and risk. • People Are the Multiplier Effect: One of my proudest achievements is coaching 30+ team members into leadership and cross-functional roles. When people grow, businesses grow. Thought Leadership:I actively contribute to the Customer Success and SaaS community, sharing insights on monetizing CS, optimizing customer health and aligning CS with product strategy to drive durable growth. Passion for Social Impact:Beyond business, I’m committed to making a positive social impact, particularly through initiatives that give children their best chance in life. My experience working with nonprofits, healthcare systems and mission-driven organizations reinforced my belief that technology should be a true enabler of creating a better world.Let’s Connect:When I have space, I love exchanging ideas with leaders, innovators and changemakers whether about scaling businesses, driving customer/social impact or helping organizations successfully adopt emerging technologies like AI.

Experience

1. Head of Americas Customer Success (Customer Success Lead)

   DeepL

   Jan 2025 — Present · Austin, TX, US

   I help businesses harness the power of Language AI to break down communication barriers and drive meaningful global impact. Leading a growing team of CSMs, I focus on coaching, strategic execution and cross-functional collaboration to ensure our customer realize the full value of DeepL’s solutions.With a background in scaling teams, operational transformation and customer advocacy, I thrive in creating high-performance environments where both customers and team members succeed. My role blends strategic leadership and hands-on execution. I build scalable processes, drive product adoption and strengthen partnerships across Sales, Product and Engineering to fuel long-term customer success.

Education

• The University of Texas at Austin

  BA, History

  2003 — 2006

• Suffolk University Madrid Campus

  European History and Spanish

  2006 — 2006

• Alamo Heights

  High School Diploma

  1999 — 2003

Skills

• Search Engine Optimization (SEO)
• Leadership
• Crm
• Demand Generation
• Account Management
• Customer Success
• Digital Marketing
• Marketing Automation
• Social Media
• Social Media Marketing
• B2b
• Customer Relationship Management (Crm)
• Online Advertising
• Enterprise Software
• Analytics
• Web Marketing
• Salesforce.com
• Digital Strategy
• Management
• Enterprise Risk Management
• Advertising
• Client Success
• Marketing Strategy
• Ppc
• Sem
• Lead Generation
• Customer Acquisition
• SEO
• Marketing
• Saas
• Social Commerce
• Customer Retention
• Strategy
• E-Commerce
• Email Marketing
• Web Analytics
• Online Marketing