Staff Technical Program Manager, Infrastructure Engineering
Current
2023 - Present
~3 yrs 6 mos
AeroLeads people directory · profile
Henry Cajas Email & Phone Number
Technical Program Management | Infrastructure Engineering
at
Squarespace
1 work email found
@teachable.com
4 phones found area 646, 718, and 212
LinkedIn matched
✓ Verified July 2026
4 data sources
Profile completeness 100%
Current company
Role
Technical Program Management | Infrastructure Engineering
Location
Greater Tampa Bay Area, United States
Company size
Who is Henry Cajas? Overview
A concise factual answer block for searchers comparing this professional profile.
Quick answer
Henry Cajas is listed as Technical Program Management | Infrastructure Engineering at Squarespace, a with 501 employees, based in Greater Tampa Bay Area, United States. AeroLeads shows a work email signal at teachable.com, phone signal with area code 646, 718, 212, and a matched LinkedIn profile for Henry Cajas.
Henry Cajas previously worked as Staff Technical Program Manager, Infrastructure Engineering at Squarespace and Technical Consultant at Self-Employed. Henry Cajas holds Computer Engineering from New York University - Polytechnic School Of Engineering.
Company email context
Email format at Squarespace
This section adds company-level context without repeating Henry Cajas's masked contact details.
{first_initial}{last}@teachable.com
86% confidence
AeroLeads found 1 current-domain work email signal for Henry Cajas. Compare company email patterns before reaching out.
Profile bio
About Henry Cajas
I am a challenge-driven leader with over 14 years of experience in the education technology sector. I drive success by understanding how systems are put together, and collaborating across teams and business units to achieve company goals in a sustainable manner. I have a strong background in delivering high quality business outcomes, building for scale, and working with engineers to reduce technical debt and increase system performance. By studying individual product architectures, how they interact, and their security posture at a granular technical level, I help identify future risks for business and guide long term strategy and roadmaps. By developing relationships across business units, and establishing communication flows, I increase transparency for work in flight, and build trust for my teams. I have led dozens of major cybersecurity and infrastructure projects from inception to delivery, and built or modified business processes to support them. I have led teams to build improvements for software deployment pipelines, internal customer service tools, and CRM systems. Along the way, I've built and lead teams, managed large budgets, defined policies, led compliance and legal projects (HIPAA, GDPR), and evolved vendor analysis and procurement processes. I have strong knowledge of Amazon Web Services (AWS) features and best practices and use this knowledge to guide decisions about how applications will be implemented, security considerations for the same, and to determine the build out and maintenance costs.
Listed skills include Quality Assurance, Project Management, Agile Methodologies, Jira, and 24 others.
Current workplace
Henry Cajas's current company
Company context helps verify the profile and gives searchers a useful next step.
Squarespace
12 roles · 5 years
Henry Cajas work experience
A career timeline built from the work history available for this profile.
Technical Consultant
Self-Employed
2022 - 2023
~1 yr
Director, Security Governance
Hotmart is the parent company of Teachable. Both companies build platforms that enable entrepreneurs to create digital businesses with world class tools and integrations.
Feb 2022 - Sep 2022
Director Of Product, Cybersecurity & Platform
Teachable is a subsidiary company of Hotmart. Teachable provides a platform that allows anyone to create and sell online courses and coaching, alongside a suite of tools to manage and market their business.
Feb 2021 - Feb 2022
Aug 2020 - Feb 2021
Senior Director Of Product, Customer Operations
Oversaw the establishment of the Customer Ops portfolio, which included 3 teams (CRM Engineering, Placement Systems, Core Systems) whose platform systems were at the intersection of all other technology teams within the company.Identified systems, processes, and third party vendor tools to be owned by the new portfolio as well as identified / redistributed orphaned systemsBuilt out health dashboard for systems owned by new portfolio to improve internal/ external transparencyManaged rapidly shifting priorities with senior business stakeholdersNegotiated reduction in vendor license cost for third party Salesforce toolSupervised two product managers
May 2019 - Jan 2020
Sr. Director Of Product, Devops & Cybersecurity
Worked across teams to build and secure infrastructure within AWS as the foundation that underpins 2U's technology offering and powers learning for tens of thousands of students. - Reduced maintenance overhead for DevOps team through replacement of legacy systems- Consulted on incident response protocols and participated in tabletop exercises to assess capability- Introduced additional cybersecurity sign offs for key system changes such as SFTP- Joined Enterprise Leadership Team to collaborate cross departmentally on large scale corporate challenges- Developed and implemented data lifecycle rules for several systems in cooperation with Legal / Compliance teams
Sep 2016 - May 2019
Product Development Manager, It Operations
Managed all projects in the IT Operations sphere working extensively with Amazon Web Services (AWS).Conducted technical reviews alongside Ops engineers for new projects being built by other engineering teams in order to understand their infrastructure needs and translate requirements into project plans.Maintained documentation of complex infrastructure.
Nov 2013 - Sep 2016
Release Manager
2U's first release manager responsible for all software deployments to production across all teams, rollback plans, business approvals and communication with stakeholders and impacted parties. Oversaw several successful large scale infrastructure migrations including moving across regions with minimal downtime.Worked with engineering teams to bring deployment time for key systems down from 2+ hours to 8 minutes including automated tests.Sourced and managed a QA team of 12 personnel (in-house and offshore).Oversaw the introduction and implementation of automated testing using Selenium.Implemented test case tracking system, TestRail, which tied directly to Jira for easy reporting of test case counts / statuses.Created and/or approved all deployment plans.Worked directly with other PMs and stakeholders to ensure any deployment were transparent, documented, and approved.Assisted in creation and implementation of emergency protocol; a precursor to future incident response.
Mar 2012 - Nov 2013
Product Development Manager
Owned technical implementation of learning platforms, data transfer systems, and video conferencing as part of a proprietary application suite for newly added masters degree programs in the earliest days of Online Program Management (OPM).Assisted in the technical build out and launch of the Online Master of Social Work at USC which, in 2016, became the largest social work program in the world due to the online enrollment component.Assisted in the launch of the MBA@UNC program, which has since become a top ranked online MBA program (US News 2020).Assisted in the technical launch of the Nursing@Georgetown program.Won internal design competition for a new product, Air Traffic Control - a system to view and monitor class live session schedules and active sessions, which was later built and put into production use by Faculty and Student Success teams.
Jul 2010 - Mar 2012
Technical Project Manager
Managed data migration and cutover for a social media platform of over ten thousand users to a custom ONEsite implementation. This included hands-on MySQL-based data verification resulting in full data integrity for transferred elements. Managed redesign and launch of electronic greeting cards including all testing and data validation.Integrated white label group buying platform (Groupon clone) as an additional revenue stream for the company.Managed build out of customized Sitecore CMS for email newsletters.
Jun 2007 - Jul 2010
Qa Analyst
Performed manual quality assurance testing for websites and internal tools.Identified test scenarios and created and executed test plans Used SQL queries and hand calculation to validate data for mission-critical assessment rollup reports for the largest school districts in the country
Oct 2004 - May 2007
Team & coworkers
Colleagues at Squarespace
Other employees you can reach at squarespace.com. View company contacts for 501 employees →
JK
Jenniferlouise Kellett
Colleague at SquarespaceIreland
View →
KT
Kelli Trogani
Colleague at SquarespaceNew York City Metropolitan Area, United States
View →
SR
Sarah Rivera
Colleague at SquarespaceNew York, United States
View →
CT
Clodagh Talbot
Colleague at SquarespaceIreland
View →
MR
Masud Rana
Colleague at SquarespaceSherpur, Bangladesh
View →
NP
Nicole Pikulin
Colleague at SquarespaceStaten Island, New York, United States
View →
JY
Joshua Y.
Colleague at SquarespaceSeattle, Washington, United States
View →
AL
Adam Levy
Colleague at SquarespaceNew York, United States
View →
AM
Alejandro Miyashiro
Colleague at SquarespaceNew York, United States
View →
KF
Kurt Filippone
Colleague at SquarespaceColumbus, Ohio, United States
View →
Jenniferlouise Kellett
Colleague at SquarespaceIreland
View →
KT
Kelli Trogani
Colleague at SquarespaceNew York City Metropolitan Area, United States
View →
SR
Sarah Rivera
Colleague at SquarespaceNew York, United States
View →
CT
Clodagh Talbot
Colleague at SquarespaceIreland
View →
MR
Masud Rana
Colleague at SquarespaceSherpur, Bangladesh
View →
NP
Nicole Pikulin
Colleague at SquarespaceStaten Island, New York, United States
View →
JY
Joshua Y.
Colleague at SquarespaceSeattle, Washington, United States
View →
AL
Adam Levy
Colleague at SquarespaceNew York, United States
View →
AM
Alejandro Miyashiro
Colleague at SquarespaceNew York, United States
View →
KF
Kurt Filippone
Colleague at SquarespaceColumbus, Ohio, United States
View →
2 education records
Henry Cajas education
Computer Engineering
New York University - Polytechnic School Of Engineering
Electrical Engineering
State University Of New York At Farmingdale
FAQ
Frequently asked questions about Henry Cajas
Quick answers generated from the profile data available on this page.
What company does Henry Cajas work for?
Henry Cajas works for Squarespace.
What is Henry Cajas's role at Squarespace?
Henry Cajas is listed as Technical Program Management | Infrastructure Engineering at Squarespace.
What is Henry Cajas's email address?
AeroLeads has found 1 work email signal at @teachable.com for Henry Cajas at Squarespace.
What is Henry Cajas's phone number?
AeroLeads has found 4 phone signal(s) with area code 646, 718, 212 for Henry Cajas at Squarespace.
Where is Henry Cajas based?
Henry Cajas is based in Greater Tampa Bay Area, United States while working with Squarespace.
What companies has Henry Cajas worked for?
Henry Cajas has worked for Squarespace, Self-Employed, Hotmart, Teachable, and 2U.
Who are Henry Cajas's colleagues at Squarespace?
Henry Cajas's colleagues at Squarespace include Jenniferlouise Kellett, Kelli Trogani, Sarah Rivera, Clodagh Talbot, and Masud Rana.
How can I contact Henry Cajas?
You can use AeroLeads to view verified contact signals for Henry Cajas at Squarespace, including work email, phone, and LinkedIn data when available.
What schools did Henry Cajas attend?
Henry Cajas holds Computer Engineering from New York University - Polytechnic School Of Engineering.
What skills is Henry Cajas known for?
Henry Cajas is listed with skills including Quality Assurance, Project Management, Agile Methodologies, Jira, Web Applications, Agile Project Management, Scrum, and Sql.
Find 750M verified contacts
Search by job title, company, industry, location, and seniority. Export verified B2B contact data when you need it.
Start free trial