EngageSmart (ESMT) a newer name that popped up with unusual action on 3/29 as 2000 September $25 calls bought $2.75 to $2.80 to open in a large block as the first notable trade in the name and only real open interest. ESMT came public in September 2021 and traded up near $40 before working lower to a bottom near $17 a bull weekly engulfing candle in mid-March. ESMT is a leading provider of vertically-tailored customer engagement software and integrated payments capabilities. The Enterprise Solutions segment focuses across five core verticals: Health & Wellness, Government, Utilities, Financial Services, and Giving. Its simplify and automate mission-critical workflows such as scheduling, client onboarding, client communication, paperless billing, and electronic payment processing. ESMT estimates a $28B TAM with $10B for SMB Solutions and $18B in Enterprise. ESMT has a market cap of $3.75B and currently trades at a premium valuation of 12X EV/Sales though already profitable with 13% Adjusted EBIT margins and 9.2% FCF margins. ESMT key metrics include 124% dollar-based net retention rate and LTV:CAC of 11X. ESMT’s software is mission critical which leads to high retention rates. Forecasts call for revenue growth around 30% annually the next 3-5 years with SimplePractice and Invoice Cloud products gaining strong traction. ESMT is in hyper-growth mode and is currently serving less than 1% of its market opportunity. SimplePractice started as a focus in Mental Health but has seen traction across many wellness verticals with tremendous future potential. Management sees EBITDA margins above 30% longer-term but is focused on product development currently. Analysts have an average target of $31 with short interest elevated at 11.6% of the float. Citi raised its target to $30.50 after the latest quarter citing a healthy Q4 beat and strong outlook.