How to Break into Enterprise & Go Upmarket from a 2x Startup CRO turned SaaS CEO

Tushar Makhija is the co-founder and CEO of TeamOhana, a workforce intelligence platform that unifies finance, HR, and talent data, so growing companies can plan and manage headcount in real-time.In this episode, Tushar shares how TeamOhana is breaking into enterprise deals while still winning $15K mid-market accounts, and why he believes spreadsheets are the silent killer of scale.Topics we cover in this episode:- Why $15K is the minimum price even for tiny teams- What most SaaS founders get wrong about Workday- From 150 to 15,000 employees: scaling up-market without losing speed- The strategic manifesto Tushar wrote before writing code- Why spreadsheet workflows kill growth (and how to replace them)- How to build multi-product from day one without losing focus- Case study: landing Scale AI with a 30-day exit clause- Why you should produce your own founder podcast (and send it to every hire)- The LinkedIn + long-form strategy driving brand and pipeline- How TeamOhana frames “collaborative workforce intelligence” to win dealsConnect with Tushar:LinkedIn: https://www.linkedin.com/in/tusharmakhija/TeamOhana: https://teamohana.comConnect with me:LinkedIn: https://www.linkedin.com/in/finnthormeier/Website: https://www.project33.io/Podcast: https://open.spotify.com/show/03CXzsZp7wdqIRVDcqPTFH Don’t forget to subscribe for more founder-led marketing playbooks from high-growth SaaS leaders.Chapters00:00 Why TeamOhana starts every deal at $15K02:01 The hiring spreadsheet every company hates05:10 Why selling to both Finance and HR was non-negotiable08:30 Breaking into enterprise: from mid-market to 15K+ employees10:40 How Tushar priced for scale (and resisted the $1K/month trap)14:20 Building a multi-product platform with a narrow start18:30 Turning spreadsheets into cloud-native workflows22:00 The playbook for converting $15K logos into $100K ACVs24:10 How Scale AI became a customer with a 45-day escape clause28:30 Competing with Workday: why they’re a filing cabinet, not a system of action32:50 Why hiring managers must live inside your product35:00 GTM channels: website, LinkedIn, outbound—and one long-form bet38:00 The 2-hour podcast Tushar made himself (and why he did it)41:00 Every new hire watches the founder video—here’s why42:45 Final advice: pick 2–3 channels and go deep#linkedin #founderledmarketing #linkedinads #linkedinagency #founderbranding #saas #b2bmarketing #demandgeneration #demandgen #content #b2b #revenue #contentmarketing #performancemarketing #videomarketing #personalbranding This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.executivebrand.org