Enterprise revenue & go-to-market

Great technology.
Lasting business.

I’m Kerry Ancheta. I turn technical adoption into enterprise revenue—and build the teams, commercial models, and operating systems to scale it.

Open source. Cybersecurity. Enterprise software.
A career connecting product, customers, and revenue.

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.Image created with AI from my portrait.

Experience across

MySQL

Helped commercialize open source and develop multiple go-to-market approaches.

MongoDB

Helped establish the initial sales team and hired its first sellers.

HAProxy

Launched the enterprise subscription model and developed the go-to-market approach.

OffSec

Built enterprise B2B go-to-market from an online training business and expanded internationally.

Read the case study

Additional sales and go-to-market leadership at HackerOne and Conductor.

Enterprise B2B

OffSec go-to-market transformation

Built from an established online training business.

$0 → $3.8M

HAProxy enterprise revenue

In two years, without outside funding.

85 people

Global revenue organization at OffSec

Sales, customer success, and revenue operations.

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.

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

Open a topic to explore
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.

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.

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?

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 helped shape enterprise open-source commercialization. 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

Built a technology-enabled home-services business, connecting subscriptions, pricing, customer experience, and field operations.

2018–2022

OffSec

Chief Revenue Officer

Built enterprise B2B go-to-market and an 85-person global revenue organization.

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.

2002–2010

MySQL · Oracle

Sales leadership

Helped connect developer adoption to enterprise commercialization, then led Americas sales for the acquired MySQL business.

04 / Start a conversation

What are you
building next?

A new commercial model, a stronger revenue organization,
or a clearer view of what’s holding growth back.