Enterprise revenue & go-to-market

Great technology.
Lasting business.

I’m Kerry Ancheta. Three times, I’ve built the enterprise go-to-market strategy behind a product engineers already loved: MySQL, HAProxy and OffSec. I turn technical adoption into revenue, then build the team, commercial model and operating system to scale it.

Open to go-to-market and revenue leadership roles at growth-stage cybersecurity and technology companies

25 years building startups in cybersecurity, open source, and developer and infrastructure software, and moving them to recurring revenue.
A career connecting product, customers, and revenue, with successful teams across enterprise, ISV, OEM, inside sales, BDRs and channel partners.

AI-created presenter image of Kerry Ancheta standing beside a whiteboard connecting forecasting, ideal customers, sales systems, go-to-market, pricing and packaging, metrics, and diagnostics.
THE PIECES HAVE TO WORK TOGETHER.

The record

MySQL

Zero to a $1B acquisition

Built the North American enterprise business on top of free open source, with 79% of bookings in recurring subscriptions, before MySQL’s $1B acquisition by Sun.

Read the case study

HAProxy

$0 → $3.8M in two years

Designed and launched the first enterprise subscription model and built the first sales team, with no outside funding.

OffSec

Over plan three years running

Transformed pure web ecommerce into a diversified global business across enterprise, Fed/SLED, mid-market, and web sales, selling direct and through channel partners.

Read the case study

MongoDB

First sales team

Hired and mobilized the first sellers, set the initial customer profile and value proposition, and secured early enterprise design wins.

Additional sales and go-to-market leadership at HackerOne and Conductor (Business Diagnostics case study).

3.5 years

OffSec business transformation

Pure web ecommerce to a diversified global business.

$12M → $54M

OffSec revenue baseline to target

Enterprise, Fed/SLED, mid-market, and web. Direct and channel sales.

85 people

Global revenue organization at OffSec

Sales, customer success, and revenue operations.

25 years building startups, and moving them to recurring revenue.

Infrastructure & data

MySQL
~$1B acquisition, now part of Oracle
MongoDB
IPO
Conductor
Acquired by WeWork
HAProxy
Privately owned, built without outside funding

Cybersecurity

HackerOne
Backed by Benchmark
OffSec
Private-equity backed, then sold to a second PE firm in 2024

Where these companies went, including after my time there.

“Kerry has over delivered his sales goals 3 years in a row ever since he started at OffSec.”

CEO of OffSec · 2021 executive review, rated Best in Class for vision, strategy and performance

“I value Kerry’s thought partnership, his analytical rigor, his pushback based on data, facts, experience.”

CEO of OffSec

Cybersecurity

Security sales start with the practitioner.

I’ve led revenue at two cybersecurity companies, OffSec and HackerOne, selling to practitioners, enterprise security teams and government.

Security works a lot like open source. Adoption starts with the practitioner: the pentester earning a certification, the researcher reporting a bug. The enterprise business comes from finding the team behind that person and selling to the leaders responsible for it.

  • OffSec

    Chief Revenue Officer · 2018–2022

    Led revenue for the company behind the OSCP certification and Kali Linux. Built enterprise and government sales on top of a web ecommerce business, with customers including Deloitte and the U.S. Army, and workforce programs with government and universities in Saudi Arabia.

    Read the case study
  • HackerOne

    Head of Sales, interim · 2015–2016

    Rebuilt sales and marketing for the hacker-powered security platform during a major product launch, then helped recruit and transition to a permanent CRO.

Where I do my best work

Go-to-market leadership, from the first sellers to scale.

  • 01

    Small to sizable, more than once. I’ve built enterprise revenue from the first deals into established revenue organizations at MySQL, HAProxy and OffSec. The best fit is a growth-stage company with product-market fit.

  • 02

    Range across go-to-market models. Open source and proprietary, product-led and enterprise, direct, channel, OEM, ISV and government. I bring what fits your business, not the last company’s playbook.

  • 03

    Analytical, and at home in complexity. I measure the funnel from first touch to renewal, find the real constraint, and simplify the sales motion so the team can execute.

  • 04

    Revenue has to work with product and marketing. Packaging, differentiation and the story to market need to be built together.

01 / How I think

A sales system.
Working together.

Markets, commercial models, people, and operating systems have to work together. Each decision shapes the others, from the first sellers to a more specialized organization.

How I scale a business

  1. Repeatability. Map the customer journey so the team can win the same way twice.
  2. Systems & process. Instrument the whole funnel, from first touch through renewal and expansion.
  3. Unit economics. Know what each customer costs to win and is worth over time, then scale what pays back.

These are the responsibilities I connect when building and leading technology revenue businesses.

01Markets & ideal customers

Understand the organization behind the buyer.

An ideal customer profile needs more than company size and industry. I look at the use case, buying trigger, technical environment, buying group, and the value that makes a purchase worthwhile.

At OffSec, individual training purchases often revealed larger teams with broader cybersecurity responsibilities. That helped shape our enterprise sales approach.

The question: Where does customer evidence point to a repeatable opportunity?

02Go-to-market strategy

Connect market choices to the way the business operates.

Choose the segments, sales approaches, coverage, and partnerships that fit how customers buy. Then identify the people, commercial terms, and delivery capabilities required to support those choices.

I treat new segments and routes to market as experiments: a small team, a clear hypothesis and an agreed measure of success. We scale what works and adjust what doesn’t.

My work at OffSec included developing an enterprise B2B business and adding specialized coverage as the markets and opportunities developed.

The question: What must we build to win and serve this market?

Explore this approach ↗

03Pricing & packaging

Shape the commercial offer together.

I work closely with marketing on positioning, pricing, and packaging. The offer needs to express customer value and support the sales approach, while remaining understandable to buyers.

At MySQL, the free edition set the bar. The paid subscription had to earn its price with capabilities the community version lacked, so I pushed product and marketing to build and explain that difference.

Volume, contract terms, renewals, and expansion connect the commercial model to sales, product, finance, and customer success.

The question: Does the offer fit the customer’s value and buying process?

04Building & leading teams

Develop the people the next stage requires.

I start close to the work: hiring and training early sellers, joining calls, and coaching. As the business develops, I add management, prospecting support, and specialist coverage.

Shared expectations, feedback, and useful operating routines help people perform. The organization needs to evolve as the market and product portfolio change.

The question: What does the team need to perform now, and lead the next stage?

05Sales execution & systems

Make the process useful in the daily work.

Qualification, stage criteria, CRM, account ownership, and handoffs need consistent definitions and clear responsibilities. The system should support the work and make problems visible.

At OffSec, I negotiated and implemented the initial Salesforce setup, then hired specialist support and connected the sales methodology to forecasting and pipeline development.

The question: Does the process help sellers, managers, and customers move forward?

06Pipeline & forecasting

Build the opportunity base and assess it with evidence.

Pipeline development starts with the right customers and clear qualification. Forecasting depends on observable buyer progress, commitments, realistic timing, and a shared definition of each stage.

Review movement, conversion, and slippage by segment and seller. Use what the team learns to improve the approach and the forecast.

The question: What evidence supports this opportunity, its timing, and the next step?

07Customer growth & renewals

Connect commercial ownership to customer value.

A signed contract begins the next part of the relationship. Clear handoffs and a shared understanding of customer goals help sales and customer success work together on adoption, renewals, and expansion.

At OffSec, sales owned commercial renewal and expansion conversations, working with customer success on engagement and program health. We tracked renewals separately from new business.

The question: Is the customer getting value, and what should happen next?

08Metrics & business diagnostics

Find the constraint before prescribing the fix.

Connect pipeline, conversion, sales-cycle length, deal value, repeat purchasing, and expansion. Use consistent definitions and segment views that help explain performance.

When a number changes, distinguish volume from customer mix, confirm the data, and test a specific explanation. The measure should lead to a decision.

The question: Where does the evidence say the business is getting stuck?

A point of view

When the product is free, sales starts with differentiation.

If people can use your product for free, you have to give them compelling reasons to pay. A subscription business built on open source works only when the paid product is meaningfully different from the free one.

I learned that leading MySQL’s enterprise business. We beat our numbers, but the ceiling we kept hitting wasn’t the sales team. It was how clearly the paid product stood apart from the free one.

Sales can’t create that difference alone. Since MySQL, I’ve worked hand in hand with product management and marketing to build real differentiation into the offer, then tell that story clearly to the market. It’s the first thing I look at in any company where adoption is ahead of revenue.

Read the MySQL story
Kerry Ancheta seated in his office, smiling.
Kerry Ancheta · New York City Metro

02 / A little background

A builder, from the
model to the team.

I’ve spent my career helping technical companies turn adoption into durable enterprise businesses.

At MySQL, I built the North American enterprise business on top of a free, open-source database. At HAProxy, I designed and launched the first enterprise subscription model and built the initial sales team. As CRO at OffSec, I built a global revenue organization and developed enterprise B2B sales from an established online training business.

My work spans databases, networking, cybersecurity, cloud platforms, and enterprise software. It includes building teams, hiring and developing leaders, structuring multimillion-dollar deals, and connecting sales execution to product strategy and customer value.

At Handy Homes, I brought that experience into a technology-enabled services business. I built and led a four-engineer team, learned AI-assisted development alongside them, and helped release two mobile apps. That experience keeps my interest in AI grounded in the daily work of building and operating a business.

Read the full résumé

03 / The work behind the perspective

Built in the field.

Download résumé

2023–2026

Handy Homes

Chief Executive Officer

I founded and built a technology-enabled home-services business, connecting subscriptions, pricing, customer experience, and field operations. We built two mobile apps connected to Salesforce through its APIs, and used AI to instrument how the business ran day to day.

2018–2022

OffSec

Chief Revenue Officer

In 3.5 years, transformed pure web ecommerce into a diversified global business across enterprise, Fed/SLED, mid-market, and web sales, selling direct and through channel partners. Case study ↗

2016–2018

HAProxy Technologies

Chief Revenue Officer

Designed the enterprise subscription model and grew revenue from zero to $3.8M in two years.

2010–2016

HackerOne · Conductor
Apprenda · MongoDB

Sales & go-to-market leadership

Built early enterprise teams, refined sales operations, and led organizations through different stages of growth. At Conductor, rebuilt the sales engine and measured the whole funnel, from first touch to renewal, to find the real constraint on growth. Conductor case study ↗

2002–2010

MySQL · Sun · Oracle

Vice President of Sales, North America Enterprise

Built the enterprise business behind the world’s most popular open-source database, from zero to mostly recurring subscriptions. After Sun’s $1B acquisition, led MySQL sales for the Americas through Oracle’s purchase of Sun. Case study ↗

04 / Start a conversation

Looking for my
next leadership role.

I’m talking with growth-stage cybersecurity and technology companies that need strong go-to-market leadership for their next stage of growth.

Hiring managers and recruiters: email is the fastest way to reach me.