Sai Cheekireddy

Sai Cheekireddy Consulting · Chicago, IL · Hybrid

• Advise 5 SaaS companies across product adoption, customer education, enablement, and self-service, partnering across Product, Growth, Customer Success, and GTM.
• Design in-app onboarding, Pendo experiences, and self-service education that cut time spent on repetitive support tasks by 50%+ through better guidance and automation.
• Develop learning programs for hundreds of learners, implementing Canvas and later migrating to Mindtickle as program needs matured; use AI and automation to accelerate content, analysis, and GTM workflows.

Tegus / AlphaSense · Chicago, IL · Hybrid

• Built Tegus’s GTM learning infrastructure from the ground up, implementing and administering Highspot for 100+ GTM employees across onboarding, learning paths, content, permissions, and reporting.
• Reduced new-hire ramp from ~90 days to as little as 45 days through self-paced learning, live training, office hours, and 1:1 coaching.
• Led enablement through Tegus’s acquisition by AlphaSense, updating playbooks, objection handling, sales resources, and 50+ learning assets as the product, positioning, and sales motion evolved.

ActiveCampaign · Chicago, IL · On-site

• Designed self-service onboarding and product education for a SaaS platform serving 100,000+ customers, spanning in-app guidance, videos, live learning, and digital resources.
• Scaled employee, customer, and partner certification programs reaching thousands of learners, creating assessments, interactive workbooks, learning content, and recurring study halls across the country.
• Analyzed learner behavior, feedback, and cross-functional insights from Product, Sales, Support, and Customer Success to improve education and help customers and partners adopt, sell, and support the product more effectively.

ShipBob · Chicago, IL · Hybrid

• Progressed from Sales into Enablement and Growth after consistently achieving 110%+ of quota, using firsthand customer insights to help build ShipBob’s first scalable self-service onboarding motion.
• Designed onboarding and lifecycle experiences across Pendo, Intercom, email, live education, and self-service resources, reducing reliance on high-touch Sales and Support as the Growth motion scaled.
• Grew self-service to 30%+ of sales revenue by using customer behavior and support data to improve activation, automate repeatable experiences, and enable Sales to focus further upmarket.