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How we Bootstrapped to $10m in ARR with 140% NDR

... a Robust Testimonial Machine, and Enterprise Customers Paying More than $100k/yr

Jay Hakami · Skypad

Published September 1, 2022
About this resource

Jay Hakami, CEO of Sky IT shares his $10 Million Bootstrapped playbook:

- Secrets to 140% net dollar retention

- How they hit key revenue targets

- Key Metrics they focus on and why

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What you’ll learn

Jay Hakami describes finding a retail-data problem, turning setbacks into customer opportunities, and expanding Skypad through large retailer relationships. He contrasts SaaS compensation and operating metrics with the earlier systems-integrator business.

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Key moments

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Find an unmet retail need

“KPIs that we look at as a business that may help you down the road. Um our growth, we started back in 2010. And um it's a interesting It's a beautiful graph. It goes up and hopefully will continue to to do so. Uh we're bootstrap. We did not take any outside money. Uh not from the banks, not from anyone. I own 100% of the company. Um and basically we we”

Turn a setback into an opportunity

“Um once you once you deal with um once you deal with um retailer or a brand and you don't succeed, everybody else knows. The second hiccup we had was Neiman Marcus. So, think about this for a second. Just imagine, you're collecting data from all these retailers, right? Um nobody has agreement with you. The retailers do not know you're collecting these data this data on behalf of the brands.”

Grow through retailer wins

“and Saks Fifth Avenue is a completely exclusive opportunity. There's nobody else. There's no other other mechanism to receive sell-through data. And not only that, they've taken the next step, which enables us again to grow, to get their buyers to look at the same app. So, now you got the buyers and the sellers looking at the same application, which is an ideal in our world, right? You got both looking at the same thing as opposed to Monday morning uh conversation back and forth.”

Set sales incentives

“people. Everything is online. You go on to the website. You log in. You put in the information. You put the credit card. And you're And you're going. Enterprise is a different story. Enterprise is when you we have company like L'Oreal that has 25 retailers across the globe that we collect and cleanse and populate data for. So, obviously, they're paying a much bigger a bill than billing billing billing billing, Henry. Um a much bigger bill than um than someone who's only using us for one retailer.”

Track the business lifecycle

“Logo or revenue? Uh revenue. Revenue. Uh you know I I don't even track logos. I really track by revenue. Um you know why? Because the revenue pays for the milk in the refrigerator. Logos is high fives, you know. Um so during the pandemic what we did is we befriended our brands. We said, "Listen, I know you're going through some hard times. Here's a couple of months of reduced rates. Um how else can we help you?" We got a”

The first signed deal

“SkyITGroup.com Revenue Growth 2010 2013 2015 2016 2017 2018 2019 Brand Dashboard Retail Dashboard Brands Add-On 1st Partnership Investment Signed First Deal Napkin brainstorm JULY 2010”

Recovering from churn

“How we managed churn… 2010 2013 2015 2016 2017 2018 2019 Brand Dashboard Retail Dashboard Brands Add-On”

A cease and desist turned customer

“SkyITGroup.com Revenue Growth 2010 2013 2015 2016 2017 2018 2019 Brand Dashboard Retail Dashboard Brands Add-On 1st Partnership Investment Neiman Marcus Cease and Desist …turned to customer 2018”

The first sales forecast

“2) Hitting key revenue targets 2010 2013 2015 2016 2017 2018 2019 Brand Dashboard Retail Dashboard Brands Add-On ACCIDENT 2 SALES REPS FULL SALES TEAM Our First “Sales Forecast” …from my moleskin notebook 2016”

Three growth levers

“3 Tactics Used to Hit $1m, $5m, and $10m Evolving Over the Years $1m - Chaos $5m - 1st Partnership Not Exclusive Freemium to some $10m - a BRAND What were key terms on this first partnership?”

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Resource files

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  • 2022 EOY Booking Strategy

  • How we Bootstrapped to $10m in ARR with 140% NDR - Slide Deck

About the speaker
Jay Hakami

Jay Hakami

President and CEO · Skypad

Jay Hakami is the Founder, President, and CEO of Sky IT Group a 20-year-old global SaaS data collection, distribution and insights solutions provider, headquartered in NYC. With over 30 years of successful executive leadership roles which have always focused on in-depth understanding of business challenges and solving them with deployment of creative and practical IT solutions.

Company revenue
$10M
Team size
200

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Slide text

Find a passage in the slides and open the original deck.

21 passages

Bootstrapping Sky IT

  1. March 2022 March 2022 | Jay Hakami, CEO SkyITGroup.com Jay Hakami CEO of Sky IT $10 Million Bootstrapped … and 140% net dollar retention

  2. Over the next 20 minutes: Signed first deal Cease and desist First huge churned customer Hit $1m on accident 2 sales reps, $5m in ARR Full sales team, $10m ARR 54% MRR growth with partner Our churn Increased during pandemic End of year booking strategy 3 BIG MOMENTS HITTING $$ TARGETS 3 KEY METRICS

  3. SkyITGroup.com Revenue Growth 2010 2013 2015 2016 2017 2018 2019 Brand Dashboard Retail Dashboard Brands Add-On 1st Partnership Investment

Three defining moments

  1. 3 Big Moments Idea to action 1st customers Napkin to MVP 1st huge churn Bad news spread fast The recovery Cease and desist Action taken Seize the opportunity FIRST DEAL FIRST CHURN LEGAL THREAT

  2. SkyITGroup.com Revenue Growth 2010 2013 2015 2016 2017 2018 2019 Brand Dashboard Retail Dashboard Brands Add-On 1st Partnership Investment Signed First Deal Napkin brainstorm JULY 2010

  3. How we managed churn… 2010 2013 2015 2016 2017 2018 2019 Brand Dashboard Retail Dashboard Brands Add-On

  4. SkyITGroup.com Revenue Growth 2010 2013 2015 2016 2017 2018 2019 Brand Dashboard Retail Dashboard Brands Add-On 1st Partnership Investment Neiman Marcus Cease and Desist …turned to customer 2018

Revenue milestones

  1. 2) Hitting key revenue targets 2010 2013 2015 2016 2017 2018 2019 Brand Dashboard Retail Dashboard Brands Add-On ACCIDENT

  2. 2) Hitting key revenue targets 2010 2013 2015 2016 2017 2018 2019 Brand Dashboard Retail Dashboard Brands Add-On ACCIDENT 2 SALES REPS FULL SALES TEAM Our First “Sales Forecast” …from my moleskin notebook 2016

  3. 2) Hitting key revenue targets 2010 2013 2015 2016 2017 2018 2019 Brand Dashboard Retail Dashboard Brands Add-On ACCIDENT 2 SALES REPS FULL SALES TEAM

  4. Jay Hakami President & CEO Natan Stein VP Operations & IT Gil Hakami VP Business Development Yuriy Pritulyak Director, Production Management Anna Rodriguez Director, Research & Development Meaghan Lynch Director, Program Management Ryan Tarrant Enterprise Sales Joseph Cassidy Controller Kassandra Rodriguez Business Analyst Devon Reid Account Manager Haley Ishida Sales & Marketing Operations Tina Hoang Strategic Account Manager Hana Saljanin BA Team Lead Janet Zhang BI Developer ETL Analyst Squad Sales Production Jacky Kwok Accounting Artem Morozov Production Engineer Katherine BondyBusiness Analyst Software Development Shuting Ma BI Developer Kirill Zayarniy QA Team Lead Yaroslav Shmyrko Production Team Lead Valeriy Tokalenko Production Programmer Marketing Sergii Kovtun Production Engineer Yuliya Kuzmenko QA Engineer Yurii Verstov Production Engineer Zlata PlotnikovaBI Developer Nick BaldwinBusiness Analyst Fred Schlossberg CFO Ajay Bhandari Senior Developer Sydney DooleyInt. Business Analyst Caitlin GuntnerInt. Business Analyst Vladyslav Kanievskyi Production Engineer Vadim SamoilenkoQA Engineer QA Account Management Accounting Ali Keech Retail Partnership Program Manager Pravallika Rao MedavarapuQlik Developer Vasiliy MishinskiyQA Engineer Chaya Rubinstein Senior Account Manager Danny KimBI Developer Sergii Felko Production Engineer Lana MaroufBusiness Analyst Katie ZatykoBusiness Analyst Jeanette Chen Director, Marketing Our Sales Team Today

Metrics and booking strategy

  1. 3) Key Metrics … that I focus on today 54% MRR growth with partnership strategy Managing churn during pandemic Start/End of year “Bookings Strategy”

  2. 2) Hitting key revenue targets 2010 2013 2015 2016 2017 2018 2019 Brand Dashboard Retail Dashboard Brands Add-On ACCIDENT 2 SALES REPS FULL SALES TEAM End of year booking strategy … excel template we use 2022 PLAN

  3. I just showed you: Signed first deal Cease and desist First huge churned customer Hit $1m on accident 2 sales reps, $5m in ARR Full sales team, $10m ARR 54% MRR growth with partner Our churn Increased during pandemic End of year booking strategy 3 BIG MOMENTS HITTING $$ TARGETS 3 KEY METRICS

  4. March 2022 | Jay Hakami, CEO SkyITGroup.com Jay Hakami [redacted email]

  5. Data Insights Retailers/Brands

  6. CEASE AND DESIST

Growth levers

  1. 3 Tactics Used to Hit $1m, $5m, and $10m Evolving Over the Years $1m - Chaos $5m - 1st Partnership Not Exclusive Freemium to some $10m - a BRAND What were key terms on this first partnership?

  2. Metrics and Tactics 3 Metrics I Care About Most CHURN Why? Efforts to Retain CMRR Early in the Year Sales Strategy End of the Year Sales Strategy MRR / ARR Single to Enterprise Partnerships

  3. FIRST DEAL

  4. 3 GROWTH LEVERS Take a photo and share it! @FounderPathHQ 3 GROWTH LEVERS Take a photo and share it! @FounderPathHQ Resources: Take a photo and share it! @FounderPathHQ Take a photo and share it! @FounderPathHQ 3 GROWTH LEVERS 3 GROWTH LEVERS Take a photo and share it! @FounderPathHQ Take a photo and share it! @FounderPathHQ