Skypad's CEO on turning a setback into a retailer opportunity, setting sales incentives and tracking metrics that drive 140% NDR
Jay Hakami · Skypad
Published September 1, 2022Jay 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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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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“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”
“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.”
“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.”
“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.”
“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”
“Our churn Increased during pandemic”
“How we managed churn…”
“2) Hitting key revenue targets”
“Early in the Year Sales Strategy”
Video
2022 EOY Booking Strategy
How we Bootstrapped to $10m in ARR with 140% NDR - Slide Deck
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.
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23 passages
March 2022 March 2022 | Jay Hakami, CEO SkyITGroup.com Jay Hakami CEO of Sky IT $10 Million Bootstrapped … and 140% net dollar retention
The talk follows three turning points, the path to revenue milestones, and three operating metrics. Its outline includes the first deal, a major churn event, a legal threat, sales-team growth, partner-led MRR growth, pandemic churn, and year-end bookings.
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
Sky IT Group’s plotted revenue rises from $50k in 2010 to $10m in 2022, with labeled points of $1m, $1.85m, $2.8m, $4.6m, and $7.5m along the way. The timeline places product launches and a first partnership investment alongside the growth curve.
SkyITGroup.com Revenue Growth 2010 2013 2015 2016 2017 2018 2019 Brand Dashboard Retail Dashboard Brands Add-On 1st Partnership Investment
The company’s story centers on landing its first deal, recovering after a large customer churned, and responding to a legal threat. The listed steps move from an idea and first customers to recovery and action.
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
A napkin sketch connects retailers with brands, illustrating the initial concept behind the first signed deal. The timeline marks the milestone in July 2010.
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
SkyPad brings retailer data from feeds, portals, emailed reports, ERP systems, and owned retail sources into one database. It then aligns and validates retailer metrics and item masters before presenting the results in a self-serve app, with customer support alongside it.
The dashboard is presented as the place to view topline performance statistics. This image introduces the product view that follows the data-processing diagram.
The revenue curve keeps climbing across the company’s timeline, even as the section turns to churn management. Labeled values rise from $50k at the beginning to $10m at the end, with no dip shown in the plotted series.
How we managed churn… 2010 2013 2015 2016 2017 2018 2019 Brand Dashboard Retail Dashboard Brands Add-On
A cease-and-desist demand from Neiman Marcus was followed by a partnership announcement, turning a legal threat into a customer relationship. The timeline places the episode in 2018.
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 revenue timeline labels the early $1m milestone as an accident, framing the first major target as an unexpected result. The curve then continues upward toward later revenue levels.
2) Hitting key revenue targets 2010 2013 2015 2016 2017 2018 2019 Brand Dashboard Retail Dashboard Brands Add-On ACCIDENT
Hakami’s first sales forecast was a handwritten notebook table of clients, stages, and recurring and setup revenue. The image shows a rough, account-by-account planning process rather than a formal forecasting system.
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
The timeline connects revenue milestones with the growth of the sales team, from an accidental early target to two sales representatives and then a full team. It presents team expansion as part of the company’s progress toward higher revenue.
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
The organization chart shows a broad team arranged under executive, operations, business development, and finance leadership. Sales, account management, marketing, production, software development, analytics, and accounting roles support the business.
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
The speaker focuses on partner-driven MRR growth, managing churn during the pandemic, and a start- and end-of-year bookings strategy. These are presented as current operating priorities.
3) Key Metrics … that I focus on today 54% MRR growth with partnership strategy Managing churn during pandemic Start/End of year “Bookings Strategy”
A monthly planning workbook organizes enterprise MRR projections and retailer-level increases and decreases across the year. The screenshot emphasizes tracking account changes to build a bookings plan.
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
The recap groups the story into major turning points, revenue targets, and key metrics. It revisits the first deal, churn and legal challenges, sales-team growth, partner-led MRR growth, and year-end bookings.
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
Hakami thanks the audience and closes with the SkyPad brand. The contact details invite follow-up without repeating them here.
March 2022 | Jay Hakami, CEO SkyITGroup.com Jay Hakami [redacted email]
A laptop mockup displays SkyPad’s retailer and brand data interface, positioning the product as a way to view retail information in one place. The small table suggests a product analytics view, though its individual entries are not legible.
Data Insights Retailers/Brands
A photographed legal letter shows a copyright-related demand and instructions to route the matter through legal counsel. Redacted names keep the parties unidentified in the image.
CEASE AND DESIST
The deck associates $1m with chaos, $5m with a first partnership that was non-exclusive and partly freemium, and $10m with building a brand. A prompt asks the audience to consider the partnership’s key terms.
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?
The framework pairs MRR and ARR with moving from single accounts to enterprise and using partnerships, churn with retention efforts, and CMRR with early- and late-year sales strategies. It links each metric to a practical operating focus.
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
The handwritten drawing connects multiple retailers to multiple brands, showing the original concept as a many-to-many matching problem. It is labeled as the first deal.
FIRST DEAL
A repeated set of branded prompts asks attendees to photograph and share the session. The slide serves as a social-sharing call to action and resource-card close.
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