Chris E. Caldwell
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Chris E. Caldwell Email & Phone Number

Finance Executive | Financial Operations Management | Strategic Planning & Management at eSkill
Location: San Antonio, Texas, United States 13 work roles 2 schools
1 work email found @livingsecurity.com 4 phones found area 210 and 415 LinkedIn matched
✓ Verified Jul 2026 4 data sources Profile completeness 100%

Contact Signals · 1 work email · 4 phones

Work email c****@livingsecurity.com
Direct phone (210) ***-****
LinkedIn Profile matched
3 free lookups remaining · No credit card
Current company
Role
Finance Executive | Financial Operations Management | Strategic Planning & Management
Location
San Antonio, Texas, United States

Who is Chris E. Caldwell? Overview

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Quick answer

Chris E. Caldwell is listed as Finance Executive | Financial Operations Management | Strategic Planning & Management at eSkill, based in San Antonio, Texas, United States. AeroLeads shows a work email signal at livingsecurity.com, phone signal with area code 210, 415, and a matched LinkedIn profile for Chris E. Caldwell.

Chris E. Caldwell previously worked as Chief Financial Officer at Eskill and Chief Financial Officer at Living Security. Chris E. Caldwell holds Master Of Science, Finance from The University Of Texas At San Antonio.

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Email format at eSkill

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ccaldwell@livingsecurity.com
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AeroLeads found 1 current-domain work email signal for Chris E. Caldwell. Compare company email patterns before reaching out.

Profile bio

About Chris E. Caldwell

✦ Summary ✦As an accomplished, visionary and dynamic Financial Operations executive, I bring outstanding hands-on experience defining and driving business forward with financial management strategies that consistently optimize and improve operations to deliver deep cost savings while driving revenue growth. I offer a proven record of steering and delivering organizational transformations and integrations for global initiatives of industry-leading organizations.Financial Operations Subject Matter Expert, including Global Financial Operations Management, Shared Services Partner Management, Forecasting & Financial Planning, Team Building & Development, Project Management, Process Evaluation & Improvements, and Strategic management of budgets up to $600M.I cultivate partnerships and build trusted relationships with stakeholders and executive leadership, influencing and leading key financial and business decision-making. I also bring polished communication and presentation skills, grounded in ability to translate complex financial data to easily business information.Finally I am a confident, decisive, servant leader with unparalleled ability to build, develop and lead highly effective teams, while continually assessing for opportunities to maximize revenue growth, optimize operations, and cut costs as well as drive user engagement and productivity, resulting in exceeding revenue generation expectations.✦ Areas of Expertise ✦Strategic Planning • Financial Operations Management • Project Management • Business Intelligence (BI) • Fiscal Management • Financial Analysis • P & L • General Ledger • Accounts Receivable Process Evaluations • Forecasting • Financial Planning • Treasury Management • Revenue Generation • Cost Reductions • Cost Planning • Budget Management • GAAP • Audit • KPI • Assessments & Analytics • Automation • Shared Services • Business Solutions • Partner Management • Executive Communications • Board Presentations • Negotiations • Reporting • Compliance • People Management • Team Development • Team Building • Coaching & Mentoring • Problem Solving✦ Key Achievements ✦▸ Successfully partnered with the Board of Directors on 2 rounds of investment funding equity raises▸ Led the successful sale of a capital constrained business to a strategic buyer, J2 Global, at 7x go-forward EBITDA/14x EBITDA on TTM basis▸ Reduced Customer Acquisition Costs (CAC) by 25%, resulting in improving ROI 45%▸ Transformed $3M cash burn annually to generating up to $3M annually

Listed skills include Leadership, Program Management, Cloud Computing, Marketing, and 38 others.

Current workplace

Chris E. Caldwell's current company

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eSkill
Eskill
Finance Executive | Financial Operations Management | Strategic Planning & Management
AeroLeads page
13 roles · 11 years

Chris E. Caldwell work experience

A career timeline built from the work history available for this profile.

Chief Financial Officer

Current

Chelmsford, Massachusetts, Us

Aug 2024 - Present

Chief Financial Officer

Austin, Texas, Us

Apr 2023 - Aug 2024

Vice President Finance

Austin, Texas, Us

Jun 2021 - Apr 2023

Vice President Finance

Los Angeles, California, Us

I was retained in this executive leadership role following J2’s acquisition of Inspired eLearning—a sale I engineered as CFO of Inspired eLearning. Hold full fiduciary accountability for the Inspired eLearning $12M line of business for J2 Global—a $1.5B technology company, that provides Internet services to Cloud Business and Digital Media. I preside over Inspired eLearning’s budgeting, forecasting, and financial analysis, and I’m tasked with leading implementation of the strategic synergy plan, based on the acquisition deal model—ensuring realization of expected cost savings. I also lead all integration efforts for Finance, Accounting, Pricing and Human Resources into the J2 infrastructure, as well as partnering with Cybersecurity Business Unit leaders on integration of Sales and Revenue Forecasting, and collaborating with J2’s Finance leadership on integration into J2’s ERP system.My achievements included:• Leading strategy to deliver 10% reduction in costs.• Reduced tools & eliminated multiple reporting systems.• Cut billing errors 10% and truncated billing time by 5 days.• Improved Days Sales Outstanding (DSOs) nearly 20%.• Delivered performance to budget for 2 consecutive quarters during the COVID-19 pandemic.

Nov 2020 - Jun 2021

Chief Financial Officer

New York, Ny, Us

As CFO, I held full financial accountability, including responsibility for Finance, Accounting, Treasury and Human Resource, for this $14M SaaS-based cybersecurity and awareness training company. I managed the GL, cash forecasting reporting, and budgeting—ensuring sufficient operational liquidity.My achievements included:• Successfully partnered with the Board of Directors on 2 rounds of investment funding equity raises.• Led the successful sale of a capital constrained business to a strategic buyer, J2 Global, at 7x go-forward EBITDA/14x EBITDA on TTM basis.• Secured deleveraged and improved interest rates in successfully refinancing $10M of private debt.• Led cost cutting efforts in March 2020 to ensure operational viability by transitioning from an on-hand monthly cash business to revenue generation focus.• Secured PPP Loan funds to ensure liquidity and sustainability during the COVID-19 market recession.• Reduced Customer Acquisition Costs (CAC) by 25%, resulting in improving ROI 45%.• Delivered 15% increase in revenue per user.• Restructured the accounting team, reducing by 50%, without impacting services to the business.• Revamped and streamlined the close process, reducing it 66%.• Reduced DSOs more than 25%—from 60+ days to 45 days—which improved cash flow.• Transformed $3M cash burn annually to generating up to $3M annually.

May 2019 - Nov 2020

Vice President Finance

New York, Ny, Us

Responsible for leading the company's financial strategy to drive revenue growth, expand margins and increase cash flows. Manage all aspects of Accounting, Finance and Treasury activities.

Jan 2019 - May 2020

Executive Director, Corporate Financial Planning & Analysis

San Antonio, Texas, Us

I was tapped for this executive leadership role and was tasked with steering efforts of Financial Analysts direct reports, while overseeing and ensuring the health of financial planning. My scope of leadership included monthly and quarterly financial reporting consolidation and analysis, including presentations to the Board of Directors and financial results to the external investors for this $4B+ annual revenue organization, comprised of 4 companies focused on optimizing customer relationships through multiple channels—recognized as leading providers of marketing services, transaction solutions, education services and intelligent media delivery. I also supported Shared Services functions in all matters pertaining to budgeting, planning and expense management, and I led the Corporate FP&A team, which reported to the SVP of Harland Clarke Holdings and Harland Clarke Finance. Finally, I analyzed M&A financial models for operating segments, ensuring sound financial principals were applied to accurately calculate Return on Investment (ROI).My achievements included:• Delivered performance at 100% to plan and attained 95% of revenue plan for $200M annual spend across Shared Services operations, and for $1B annual revenue plan.• Completed $4B+ in debt financing transactions, resulting in saving millions in interest and amortized loan expense by 10%.• Built the first Three Statement model to leverage understanding of capital requirements and inform senior leadership on overall financial impacts.• Automated the consolidation process, which reduced completion of financial reporting for the Board of Directors by a full day.• Played a key role in facilitating 10% reduction in G&A expense over 18 months.• Delivered 20% cost savings over 24 months by partnering with Shared Services leaders.

2016 - Jan 2019

Senior Director, Business Management

San Antonio, Texas, Us

I was promoted to steer business management of Global Marketing, and led 5 direct reports and a staff of 17, and managed $65M in annual marketing operations spend for this globally recognized cloud computing company generating $2B in annual revenue that employs 6K+ Rackers. I led all facets of operations, and was sharply focused on supporting the business unit to exceed revenue growth targets and drive improved ROI, through sound financial management and operational discipline.My achievements included:• Improved ROI 10% by shifting 25% of budgeted spend away from lower returning activities.• Re-engineered revenue models and refined benchmarking tools to accurately measure financial and operational performance, used to support the annual financial planning process and quarterly forecasting updates.• Developed team that was consistently rated as a top performing group and highly engaged as measured by semi-annual “pulse” checks.• Developed and mentored staff promoted into leadership roles.• Delivered 10% increase in closed deals.

Apr 2014 - Mar 2016

Director, Marketing Operations

San Antonio, Texas, Us

I was recruited and promoted to this leadership role to direct a staff of up to 15, while managing $65M annual spend.My achievements included:• Delivered an improved collaborative partnership with Finance pertaining to planning, budgeting and forecasting, as well as leveraged better operational support to the Marketing organization—by building and leading a centralized Operations function. • Reduced redundant tools across regions, resulting in $250K+ in savings.• Reduced time-to-market on product launches approximately 25%.

Sep 2012 - Mar 2014

Senior Manager, Business Intelligence

San Antonio, Texas, Us

I was promoted to lead a team of 4 Business Intelligence Analysts, and I managed a $65M annual spend. I also collaborated closely with analysts to set a clear vision and goals to successfully support business reporting and analytical needs.My achievements included:• Drove 100%+ increase in Partner and Marketing channel contributions to revenue.• Increased online revenue 15% without increasing spend.

Jan 2011 - Aug 2012

Manager, Financial Operations

San Antonio, Texas, Us

I was tapped for this leadership role to manage 5 Financial Analyst direct reports and held accountability for a $600M revenue plan. I also set monthly, quarterly and annual financial and operational targets for Sales, Marketing and Product, and I managed a $200M annual expense budget.My achievements included:• Managed financial aspects of $600M annual revenue operations for the U.S.• Delivered 99.5% to $600M revenue plan.• Developed and led team that ensured company performed to quota and within expense budgets for every single quarter.• Created product profitability and pricing models for new product launches, which included several services that reached $1M+ in recurring revenue in less than 12 months.• Guided Product, Sales and Marketing leadership team through the 2008-2009 recession by reducing costs 25%+ while continuing to deliver revenue growth of more than 20%.

Dec 2006 - Dec 2010

Controller

New Braunfels, Us

Managed all aspects of Marketing departments financial related activities. Provided channel analysis and ROI metrics as well as corporate level revenue forecasts.

Dec 2004 - Dec 2006

Controller And Administration Manager

San Antonio, Texas, Us

Responsible for all accounting operations activities including month-end close, financial reporting and audit processes.Led a team of 15 administrators responsible for end-to-end administrative management, including sales quoting, order management, delivery and invoicing and inventory management.

Jul 1999 - Dec 2004
2 education records

Chris E. Caldwell education

Master Of Science, Finance

The University Of Texas At San Antonio

Bba, Corporate Finance

St. Mary'S University
FAQ

Frequently asked questions about Chris E. Caldwell

Quick answers generated from the profile data available on this page.

What company does Chris E. Caldwell work for?

Chris E. Caldwell works for eSkill.

What is Chris E. Caldwell's role at eSkill?

Chris E. Caldwell is listed as Finance Executive | Financial Operations Management | Strategic Planning & Management at eSkill.

What is Chris E. Caldwell's email address?

AeroLeads has found 1 work email signal at @livingsecurity.com for Chris E. Caldwell at eSkill.

What is Chris E. Caldwell's phone number?

AeroLeads has found 4 phone signal(s) with area code 210, 415 for Chris E. Caldwell at eSkill.

Where is Chris E. Caldwell based?

Chris E. Caldwell is based in San Antonio, Texas, United States while working with eSkill.

What companies has Chris E. Caldwell worked for?

Chris E. Caldwell has worked for Eskill, Living Security, J2 Global, Inspired Elearning, Llc., and Vericast.

How can I contact Chris E. Caldwell?

You can use AeroLeads to view verified contact signals for Chris E. Caldwell at eSkill, including work email, phone, and LinkedIn data when available.

What schools did Chris E. Caldwell attend?

Chris E. Caldwell holds Master Of Science, Finance from The University Of Texas At San Antonio.

What skills is Chris E. Caldwell known for?

Chris E. Caldwell is listed with skills including Leadership, Program Management, Cloud Computing, Marketing, Strategic Partnerships, Strategy, Saas, and Salesforce.Com.

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