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 deals

Connect with Tushar:

LinkedIn: https://www.linkedin.com/in/tusharmakhija/

TeamOhana: https://teamohana.com

Connect 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.

Chapters

00:00 Why TeamOhana starts every deal at $15K

02:01 The hiring spreadsheet every company hates

05:10 Why selling to both Finance and HR was non-negotiable

08:30 Breaking into enterprise: from mid-market to 15K+ employees

10:40 How Tushar priced for scale (and resisted the $1K/month trap)

14:20 Building a multi-product platform with a narrow start

18:30 Turning spreadsheets into cloud-native workflows

22:00 The playbook for converting $15K logos into $100K ACVs

24:10 How Scale AI became a customer with a 45-day escape clause

28:30 Competing with Workday: why they’re a filing cabinet, not a system of action

32:50 Why hiring managers must live inside your product

35:00 GTM channels: website, LinkedIn, outbound—and one long-form bet

38:00 The 2-hour podcast Tushar made himself (and why he did it)

41:00 Every new hire watches the founder video—here’s why

42:45 Final advice: pick 2–3 channels and go deep

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