Deepak Gupta

Sales-led

A quota-carrying sales team is the main path to revenue.

Counts as evidence: The company describes direct sales as its primary go-to-market or reports sales headcount as the growth engine.

Who ran it

Zoom · Sales routed by deal size, land and expand · 2016 to 2020
Sales-led Supporting
Field and inside sales were organised by customer employee count and vertical, with the online channel serving smaller customers.
Zoom · Enterprise platform and AI · 2021 to now
Sales-led Primary
Enterprise customers, engaged by direct sales, resellers, or partners, went from 45.6% of revenue in fiscal 2021 to 60.3% in fiscal 2026. The sales force is now organised by subscription size, region, and vertical.
HubSpot · Naming inbound, then selling it by phone · 2006 to 2014
Sales-led Primary
Inside sales reps in Cambridge and Dublin worked the inbound leads by phone, email, and web meetings. The filings name increased sales rep capacity as the main driver of customer growth.
HubSpot · Free CRM and the first freemium products · 2014 to 2018
Sales-led Primary
Sales rep capacity was still named as the main driver of customer growth.
HubSpot · Free to Enterprise on one platform · 2018 to 2022
Sales-led Primary
The 2021 filing still names sales rep capacity, with Professional and Enterprise demand, as the driver of customer growth.
HubSpot · Beyond search: owned media and answer engines · 2022 to now
Sales-led Primary
A worldwide direct sales team still works prospects by phone, email, and web meetings, now with AI engagement tools.
Cursor · Enterprise push and consumption pricing · 2025 to now
Sales-led Supporting
By October 2026 the careers page lists a full field organisation: regional sales VPs, strategic and federal account executives, and a deal desk. Job listings show structure, not revenue mix.
Salesforce · The End of Software, sold by phone · 1999 to 2004
Sales-led Primary
Inside sales, telesales and field reps were split by company size, and small businesses were sold primarily over the phone, with website free trials among the marketing initiatives. Small businesses were about 40% of fiscal 2004 revenue.
Salesforce · AppExchange and the move to larger customers · 2004 to 2008
Sales-led Primary
The company tied its growth to medium and large businesses and expected greater costs and longer sales cycles there. Account executives stayed split across small business, general business and enterprise.
Salesforce · Many clouds, Dreamforce, Trailblazers and acquisitions · 2009 to 2024
Sales-led Primary
Direct sales stayed the main route: telephone sales in regional hubs and field sales near customers, both supported by reps who generate qualified leads.
Salesforce · Agentforce, digital labor and consumption pricing · 2024 to now
Sales-led Primary
Benioff planned 1,000 to 2,000 extra account executives just for Agentforce, because Salesforce sells direct. The 10-K adds Forward Deployed Engineers embedded in customer teams and, for the first time, lists self-service offerings beside direct sales.
Atlassian · Software that sells itself · 2002 to 2009
Sales-led Tried, then dropped
An attempt at OEM sales through one expensive, experienced enterprise salesperson failed. Farquhar calls OEM selling the antithesis of a word of mouth business model.
Atlassian · Enterprise sales on a cloud-only platform · 2022 to now
Sales-led Primary
A direct sales force of field sales and solution sales expands the largest enterprise customers. The FY2026 10-K warns that the enterprise sales motion brings higher costs, longer sales cycles, and less predictability.
Slack · Direct sales layered on self-serve, then Enterprise Grid · 2016 to 2019
Sales-led Supporting
A globally distributed field sales force, solutions engineering, demand generation, webinars, analyst relations, and C-suite events. Sales and marketing headcount grew 86% and then 77% in consecutive years.
Slack · Shared channels, the pandemic, and the sale to Salesforce · 2019 to 2021
Sales-led Primary
Customers paying more than $100,000 rose to 49% of revenue in fiscal 2021, and customers above $1M in annual recurring revenue reached 108, up 54%. Butterfield said the largest companies were choosing to standardize on Slack.
Slack · Sold by Salesforce, free tier tightened, repositioned for AI agents · 2021 to now
Sales-led Primary
Slack became part of Salesforce, which sells primarily through its direct sales force and cited synergies from combining the two companies' enterprise customer bases.
Figma · FigJam, Dev Mode, Enterprise and the Adobe deal · 2021 to 2023
Sales-led Supporting
An Enterprise plan for the largest customers launched in 2022. By 2024, about 70% of revenue came from customers on Organization and Enterprise plans.
Twilio · Inverting the enterprise sales model · 2015 to 2018
Sales-led Supporting
An enterprise sales effort with sales development, inside sales, and field sales targeted larger customers. Lawson says developers bring Twilio in first and build the prototype, then the sales force works the process through.
Twilio · Platform by acquisition and the enterprise push · 2019 to 2021
Sales-led Primary
A direct sales effort for larger customers, backed by enterprise marketing such as the Twilio Engage roadshow, which brought business leaders and developers together. Sales and marketing spend more than tripled from 2018 to 2020.
Twilio · Slowdown, split, and refocus · 2022 to 2023
Sales-led Supporting
Data & Applications got a strategic, solution-oriented sales model. A December 2023 memo filed as an 8-K says the bet on Segment go-to-market ahead of growth had not paid off, and folds Flex selling into Communications.
Twilio · Three motions, ISVs, and AI · 2024 to now
Sales-led Primary
A direct sales motion for complex, high-scale enterprises, supported by sales development, field marketing, and solution engineers. Twilio had 2,265 sales and marketing employees at the end of 2025.
Datadog · Inside sales, enterprise team, and multi-product expansion · 2016 to 2019
Sales-led Supporting
An enterprise sales team sold to large businesses from 2016, and the sales and marketing organization had 474 people by June 2019.
Datadog · Platform expansion and peak net retention · 2020 to 2022
Sales-led Supporting
The sales and marketing organization grew to about 2,300 people by December 2022.
Datadog · Usage optimization, enterprise scale, and AI · 2023 to now
Sales-led Primary
About 4,310 customers above $100,000 in ARR made up 90% of ARR at December 2025, 603 customers were above $1 million, and the sales and marketing organization had about 3,600 people.
Snowflake · Cloud data warehouse, sold on consumption · 2012 to 2018
Sales-led Primary
A direct sales force aimed at large organizations was the main route to revenue, and sales and marketing spend was 130% of revenue in fiscal 2019.
Snowflake · Land and expand, the IPO, and the Data Cloud · 2019 to 2021
Sales-led Primary
The sales force was pointed at the world's largest organizations, and from 2020 part of each commission was earned on the rate of customer consumption rather than only on signature.
Snowflake · Scaling through clouds, partners, and developers · 2021 to 2024
Sales-led Primary
Forbes Global 2000 customers became a reported key metric for the large-enterprise focus, reaching 691 by January 2024. Slootman described it as campaigning the largest enterprises globally.
Snowflake · The AI Data Cloud and agents · 2023 to now
Sales-led Primary
Direct field and inside sales, segmented by industry, size, and region, is still the main route, with resellers and distributors added. 790 Forbes Global 2000 customers contributed about 43% of fiscal 2026 revenue.
CrowdStrike · Intelligence, incident response, then one EDR product · 2012 to 2017
Sales-led Primary
The S-1 says CrowdStrike began as a large enterprise solution, and the FY2020 10-K says it and its channel partners historically sold primarily to large organizations.
CrowdStrike · Modules, trial-to-pay, marketplace and channel · 2017 to 2020
Sales-led Primary
Field and inside sales, segmented by a customer's number of endpoints, sell most subscriptions, and sales also finds existing customers for free trials of more modules. Incident response and proactive services are described as a way to cross-sell subscriptions.
CrowdStrike · Platform scale and module depth · 2020 to 2024
Sales-led Primary
The global sales team of field and inside sales is now segmented by a customer's organizational size rather than endpoint count.
CrowdStrike · After the July 2024 incident: Flex and partner-first · 2024 to now
Sales-led Supporting
A Zero Dollar Flex Fund gives qualifying new services customers 200 hours of services with no up-front cost, framed as a path to broader platform adoption. The 10-K still calls services an opportunity to cross-sell subscriptions.
Okta · Cloud SSO and enterprise sales from day one · 2009 to 2013
Sales-led Primary
Okta sold to IT buyers through field and inside sales, with cloud Single Sign-On for employees as the first product. McKinnon names go-to-market as the area he knew least.
Okta · Platform, land and expand, and the IPO · 2014 to 2017
Sales-led Primary
The sales team is divided by geography, customer size, use case and industry vertical. Sales and marketing spend was 120% of revenue in FY2015 and 91% in FY2016.
Okta · Public scale-up of the workforce engine · 2017 to 2021
Sales-led Primary
Customers above $100K in annual contract value rose from 691 at January 2018 to 1,950 at January 2021. The FY2021 10-K names land and expand with a focus on customer size and key verticals, including highly regulated sectors.
Okta · Auth0, two clouds, and security incidents · 2021 to 2024
Sales-led Primary
Customer counts still exclude customers on self-service arrangements only, and customers above $100K in annual contract value grew from 1,950 to 3,930 between FY2021 and FY2023.
Okta · Specialized sales, profitability and AI agents · 2024 to now
Sales-led Primary
Okta sellers cover IT and security buyers, including Okta Customer Identity, while Auth0 sellers focus on developers, with a hunter-farmer model in some regions. The stated strategy is to drive growth with large customers.
Anthropic · Safety lab ships an API · 2021 to 2023
Sales-led Supporting
Early API access was gated behind a request form and a follow-up from the company, not open signup.
Anthropic · Self-serve API, two clouds, plans for work · 2024 to 2025
Sales-led Supporting
The Enterprise plan added SSO, role-based permissions, and admin tooling, and was started by contacting the sales team.
Anthropic · Claude Code and the enterprise build-out · 2025 to 2025
Sales-led Primary
Anthropic appointed its first Chief Commercial Officer and a regional leadership team to drive enterprise sales expansion across key markets. The CEO says Claude Code and Claude for Enterprise are sold to enterprises as well as individual developers.
Wiz · CISO conversations, pivot, first enterprise deals · 2020 to 2020
Sales-led Primary
The founders and first hires sold directly to large enterprises before there was a sales team. The first paying customer was a Fortune 10 company, and Wiz says it landed Fortune 100 customers nine months after its first line of code. The CISO feedback calls worked as a design-partner loop and drove the pivot to cloud security.
Wiz · Agentless proof of value and the $100M sprint · 2021 to 2022
Sales-led Primary
Top-down enterprise sales to CISOs, run through proofs of value in which customers often connect their entire environment. Investors made introductions to single executives, and won accounts introduced the next ones. Wiz said it was replacing large existing solutions in every customer.
Wiz · Platform, marketplaces and partners · 2023 to 2024
Sales-led Supporting
Enterprise selling extended into the US public sector with a new Senior Director of Public Sector and a stated intent to offer a FedRAMP authorized product. Wiz for Government reached FedRAMP High authorization in September 2025.
Notion · AI in the business plans, enterprise sales, agent credits · 2025 to now
Sales-led Supporting
The co-founder and COO said in September 2025 that Notion was likely to double its sales team the following year. The careers page lists solutions consultants by segment, country general managers, and forward deployed GTM engineers. Job listings show structure, not revenue mix.
Stripe · March into the enterprise · 2020 to 2022
Sales-led Primary
The 2020 chief revenue officer hire was to lead and grow a global sales organisation as Stripe accelerated its march into the enterprise. Stripe's own letter says its startup focus had been a drawback with incumbents, and that this later inverted.
Stripe · Multi-product platform for startups and enterprises · 2023 to now
Sales-led Supporting
Enterprise is a named segment, with more than 100 companies processing over $1 billion a year. Large businesses are routed to Contact sales for custom pricing, and the 2026 leadership note describes a revenue organisation built from the ground up.
Shopify · Payments, paid search and the IPO · 2013 to 2015
Sales-led Supporting
Shopify Plus launched on February 4, 2014 for higher-volume merchants, and Shopify began hiring sales staff to sell it.
Shopify · Shopify Plus, Unite and merchant solutions take over · 2016 to 2019
Sales-led Supporting
Outbound sales for Shopify Plus, hired from early 2015, targeted larger merchants migrating off legacy platforms. Plus had about 2,500 merchants by the end of 2016 and was 27% of MRR at the end of 2019.
Shopify · Pandemic surge and a better developer deal · 2020 to 2022
Sales-led Supporting
Self-serve onboarding sat alongside outbound sales reps for Shopify Plus and POS Pro.
Shopify · Enterprise push, merchant solutions and AI channels · 2023 to now
Sales-led Primary
Commerce Components (January 2023) lets enterprise retailers adopt parts of Shopify without re-platforming. Sales and account reps sell Plus, Commerce Components and POS Pro, Plus starts at $2,300 a month, and most GMV now comes from Plus and enterprise.
Gong · Conversation intelligence, design partners, data content · 2015 to 2018
Sales-led Primary
Gong interviewed about 50 potential buyers, ran a beta with 12 design partners, then asked for a paid order in the tens of thousands, and 11 of the 12 bought. Early buyers were startups; very large companies started arriving almost in the second year.
Gong · Naming revenue intelligence, selling to the CRO · 2019 to 2022
Sales-led Primary
The rename served the sale: budget did not exist for conversation intelligence, so Gong needed the CRO, who heard the old name as a tactical tool for enablement. Pricing is a customized proposal, per user plus a platform fee.
Gong · Platform across the revenue organisation · 2023 to 2024
Sales-led Primary
Nearly 1,000 customers chose Gong as their revenue intelligence platform in the first seven months of 2023, taking the total past 4,000.
Gong · Revenue AI OS, enterprise expansion, marketplace · 2025 to now
Sales-led Primary
Growth is described in enterprise terms: half of the Fortune 10 are now Gong customers.
MongoDB · Enterprise Advanced and direct sales · 2013 to 2016
Sales-led Primary
Field and inside sales sold paid subscriptions, generally priced per server, to enterprises whose developers already knew Community Server. Customers sold by sales and partners were 96% of subscription revenue in fiscal 2016.
MongoDB · Atlas becomes the business, sold with the clouds · 2019 to now
Sales-led Primary
Direct Sales Customers were 87% of subscription revenue in fiscal 2023, and 2,799 customers paid $100K or more in ARR at January 2026. Ittycheria tells salespeople to look for where the pain is.
GitLab · Enterprise sales, partners, and the IPO · 2019 to 2021
Sales-led Primary
Selling ran in three layers: self-service, high-velocity inside sales, and outbound enterprise sales for organizations over 2,000 employees. Enterprise customers were more than 60% of ARR in FY2021, and sales and marketing cost 122% of revenue in FY2020 and 101% in FY2021.
GitLab · Pruning the cheap tier and the free ceiling · 2021 to 2024
Sales-led Supporting
Enterprise sales investment continued, and customers above $100,000 ARR rose from 492 in FY2022 to 955 in FY2024.
GitLab · AI agents and hybrid pricing · 2024 to now
Sales-led Primary
Public sector and enterprise customers were more than 70% of ARR in FY2026, and the sales organization is structured by region and size with vertical teams for regulated industries.
Asana · Up-market and top-down sales · 2023 to 2025
Sales-led Primary
Asana moved capacity toward sales-led, top-down deals with corporate and enterprise buyers, including large deals in accounts with no prior Asana use, while keeping its product-led motion.
Asana · AI Studio, credits, and the agentic platform · 2024 to now
Sales-led Primary
The FY2026 10-K calls it a bottom-up and top-down model: team adoption signals when direct sales and partners should step in to scale strategic enterprise accounts. Dan Rogers, previously CEO of LaunchDarkly, became CEO in July 2025 and chair in September 2026, and a new CRO was named to align product-led and sales-led growth.
Cloudflare · Enterprise sales layered on self-serve · 2016 to 2019
Sales-led Primary
Inside and field sales sell the Enterprise plan, and a majority of 2018 revenue came from customers they acquired. Customers with Annualized Billings over $100,000 grew from 95 at the end of 2016 to 408 by mid-2019.
Cloudflare · Contracted customers, channel and agents · 2025 to now
Sales-led Primary
A substantial majority of 2025 revenue came from contracted customers acquired by inside and field sales. Q4 2025 brought the largest contract ever, averaging $42.5M a year, and new ACV grew nearly 50%.
monday.com · More products and the move upmarket · 2021 to 2024
Sales-led Supporting
In 2024 the company emphasized mid-market customers, added account-based marketing and top-down selling, and trained sales for a sales-led strategy it said would arrive in full force in 2025.
monday.com · Hybrid sales-led GTM and the AI Work Platform · 2025 to now
Sales-led Primary
The company says its GTM shifted from performance marketing to a hybrid approach, hired a CRO, put more sellers on the ground, and rebalanced spend away from certain online channels. In July 2026 it filed a restructuring plan cutting about 20% of the workforce as part of the ongoing transformation of its product, marketing and go-to-market strategy.
Zscaler · Cloud security instead of appliances, sold with carriers · 2008 to 2016
Sales-led Primary
A sales force builds relationships with senior IT buyers in large organizations, in a joint model where a partner usually transacts the deal. The S-1 counts over 200 of the Forbes Global 2000 as customers.
Zscaler · Second product, land and expand, IPO · 2016 to 2020
Sales-led Primary
Sales and marketing ran at 60% to 70% of revenue in fiscal 2015 to 2017, with account-based marketing aimed at new enterprise accounts, and FedRAMP authorization for ZPA-Government opened the U.S. federal market.
Zscaler · The Zero Trust Exchange reframing · 2020 to 2023
Sales-led Supporting
Sales and marketing stayed the largest cost, at 68% of revenue in fiscal 2021 and 59% in fiscal 2023, and the 10-K says Zscaler sells to enterprises of all sizes.
Zscaler · Platform, flexible spend, and AI security · 2023 to now
Sales-led Primary
The sales organization is account-centric, with dedicated sales and customer success resources, and sales and marketing fell to 45% of revenue in fiscal 2026.
Vercel · AI Cloud and enterprise AI governance · 2025 to now
Sales-led Supporting
A COO hired in 2025 leads go-to-market and a CRO hired in 2026 leads a global Sales team, selling a platform for shipping apps and agents behind a company's access and security boundaries. This shows structure and intent, not revenue mix.
OpenAI · ChatGPT goes free, then paid, then to work · 2022 to 2023
Sales-led Supporting
ChatGPT Enterprise launched in August 2023 behind a Contact sales path. OpenAI said teams in over 80% of Fortune 500 companies had adopted ChatGPT, counted by accounts on corporate email domains.
OpenAI · Monetise every tier, sell through every cloud · 2025 to now
Sales-led Supporting
The business announcement routes to Contact sales, and OpenAI counts more than 1 million organizations paying through ChatGPT for Work or the developer platform.