📍 Job Overview

Job Title: Lead Technical Support Engineer
Company: Progress
Location: Belen, Costa Rica
Job Type: Hybrid (3 days on-site, 2 days remote)
Category: Technical Support & Customer Success
Date Posted: June 24, 2025
Experience Level: 10+ years
Remote Status: On-site with hybrid flexibility

🚀 Role Summary

Lead a team of technical support engineers, driving performance and ensuring customer satisfaction.
Provide expert technical support and troubleshooting for Progress' products and their integration into customer environments.
Collaborate with customers and internal teams to identify, analyze, and resolve complex technical issues.
Mentor and train new hires, and contribute to the team's knowledge base and best practices.

📝 Enhancement Note: This role requires a strong technical background, excellent communication skills, and a proven track record in leading teams to deliver exceptional customer support in a fast-paced, changing environment.

💻 Primary Responsibilities

Technical Support & Troubleshooting: Assist customers and technical support engineers in resolving complex technical issues related to Progress' products and their integration into customer environments.
Mentorship & Team Leadership: Mentor and train new hires, and provide guidance to junior team members. Identify potential issues and initiatives, and drive team performance.
Customer Relationship Management: Build and maintain strong customer relationships through effective communication, problem-solving, and customer-focused support.
Knowledge Base Management: Contribute to the team's knowledge base by creating and validating technical articles, ensuring the information is accurate, up-to-date, and meets content guidelines.
Performance Metrics & Reporting: Monitor and report on key performance indicators (KPIs) such as team average CSAT scores, case resolution times, and other relevant metrics.

📝 Enhancement Note: This role requires a balance of strong technical expertise, excellent communication skills, and the ability to work independently and collaboratively to drive team performance and customer satisfaction.

🎓 Skills & Qualifications

Education: Bachelor's Degree or equivalent experience in a relevant field, such as Computer Science, Information Technology, or a related discipline.

Experience: At least 8 years of experience in a support role within the service industry, with a strong focus on technical troubleshooting and customer support.

Required Skills:

Expertise in computing (Mac & PC), networking, and web browsers.
Solid knowledge of Windows Server roles and features, IIS, AD, DNS, and file servers.
Proficiency in Microsoft Office suite, including Outlook, Excel, PowerPoint, and Word.
Strong troubleshooting skills and the ability to analyze complex problems.
Excellent verbal and written communication skills in English.
Ability to work a fixed schedule from 12:00 pm ET to 9:00 pm ET.
Customer-focused mindset and the ability to deliver a world-class customer experience.
Ability to de-escalate customers in challenging circumstances.
Expertise in a data-driven, metrics-oriented environment.
Keen interest in Software-as-a-Service (SaaS).

Preferred Skills:

Ability to setup and troubleshoot Storage Zone Controllers, SSO, and load balancers with little guidance from documentation.
Solid knowledge of load balancing technologies and NAS devices.
Solid knowledge of identity providers and SAML 2.0 (Azure, OKTA, ADFS).
Basic SQL knowledge with the ability to use already created queries to gather data from the database.
Good command of workflow automation and the ability to troubleshoot complex workflows.
Knowledge of JavaScript, Python, and PHP, API calls.
Ability to analyze complex logs and conditional calculations.
Ability to create and use API calls using Postman or other tools.
Solid knowledge of troubleshooting web application issues.
Solid knowledge about security certificates.

📝 Enhancement Note: Candidates with experience in server administration, networking, and programming languages will have a significant advantage in this role.

📊 Web Portfolio & Project Requirements

Portfolio Essentials:

A well-structured portfolio showcasing your technical support and troubleshooting expertise, with a focus on complex problem-solving and customer success stories.
Examples of your mentoring and leadership skills, such as training materials or team performance improvement initiatives.
Demonstrations of your ability to create and maintain technical documentation, such as knowledge base articles or user guides.

Technical Documentation:

Case studies or project reports demonstrating your ability to analyze complex technical issues and provide effective solutions.
Examples of your performance metrics and reporting, highlighting your ability to track and improve key performance indicators.
Documentation of your experience with Progress' products, including any certifications or training completed.

📝 Enhancement Note: While a portfolio of technical support and troubleshooting projects is essential, candidates should also emphasize their leadership and mentoring skills, as well as their ability to create and maintain technical documentation.

💵 Compensation & Benefits

Salary Range: The salary range for this role is estimated to be between $70,000 and $90,000 USD per year, based on regional market data for senior technical support roles in Costa Rica. This estimate takes into account the candidate's experience level, the company's size, and the location's cost of living.

Benefits:

Health insurance plan covering medical services, dental, emergency care, and preventative care for employees, their spouses, and dependent children.
Life and disability insurance for employees.
Competitive salary, bonus or commission (according to the position), and best-in-class Employee Stock Purchase Program (ESPP) with a 27-month lookback.
Paid time off, including a paid day off for the employee's birthday and company holidays, as well as various leave plans.

Working Hours: This hybrid role requires working on-site for 3 days a week and remotely for 2 days a week. The on-site schedule is from 12:00 pm ET to 9:00 pm ET, with a 1-hour lunch break.

📝 Enhancement Note: The provided salary range is an estimate based on market data and should be verified with the hiring organization. The benefits package is comprehensive and designed to support employees' well-being and professional growth.

🎯 Team & Company Context

Company Culture:

Industry: Progress operates in the software industry, focusing on providing tools for developing, deploying, and managing responsible, AI-powered applications and experiences.
Company Size: Progress is a mid-sized company with a global team, providing opportunities for collaboration and growth.
Founded: Progress was founded in 1981, with a rich history in the software industry and a strong commitment to innovation and customer success.

Team Structure:

The technical support team consists of experienced technical support engineers, led by the Lead Technical Support Engineer.
The team works closely with internal stakeholders, such as product management, engineering, and sales, to ensure customer satisfaction and drive product improvement.
The team follows Agile methodologies, with a focus on continuous improvement and customer-centric problem-solving.

Development Methodology:

The technical support team follows Agile methodologies, with a focus on iterative development, customer feedback, and continuous improvement.
The team uses collaborative tools and platforms to manage cases, track progress, and maintain a knowledge base.
The team works closely with other departments to ensure that customer feedback is incorporated into product development and improvement efforts.

Company Website: Progress

📝 Enhancement Note: Progress is committed to fostering a diverse and inclusive work environment, with a strong focus on customer success and continuous improvement. The company's culture values collaboration, innovation, and a customer-centric approach to problem-solving.

📈 Career & Growth Analysis

Technical Support Career Level: This role is a senior-level position within the technical support and customer success career path. The Lead Technical Support Engineer is responsible for driving team performance, mentoring junior team members, and ensuring customer satisfaction. This role provides opportunities for growth into management or specialized technical roles within the organization.

Reporting Structure: The Lead Technical Support Engineer reports directly to the Director of Technical Support and works closely with other department heads, such as product management, engineering, and sales, to ensure customer satisfaction and drive product improvement.

Technical Impact: The Lead Technical Support Engineer plays a crucial role in ensuring customer satisfaction and driving product improvement by providing expert technical support and troubleshooting, as well as contributing to the team's knowledge base and best practices.

Growth Opportunities:

Technical Leadership: As the Lead Technical Support Engineer gains experience and demonstrates strong leadership skills, they may have the opportunity to move into a management role, such as a Technical Support Manager or Director of Technical Support.
Specialized Technical Roles: With a strong technical background and a proven track record of success, the Lead Technical Support Engineer may have the opportunity to move into a specialized technical role, such as a Senior Technical Support Engineer or Technical Support Architect.
Product Management: As the Lead Technical Support Engineer gains experience working with customers and internal stakeholders, they may have the opportunity to move into a product management role, focusing on driving product improvement and customer success.

📝 Enhancement Note: The Lead Technical Support Engineer role provides significant opportunities for career growth and development within the technical support and customer success career path. Candidates with strong technical expertise, excellent communication skills, and a proven track record of success in leading teams to deliver exceptional customer support are well-positioned to succeed in this role and advance their careers within the organization.

🌐 Work Environment

Office Type: The Progress office in Belen, Costa Rica, is a modern, collaborative workspace designed to facilitate teamwork and innovation. The office features multiple meeting rooms, open workspaces, and dedicated areas for quiet work and reflection.

Office Location(s): The Progress office is located in Belen, Costa Rica, with easy access to public transportation and nearby amenities.

Workspace Context:

Collaborative Work Environment: The office is designed to encourage collaboration and teamwork, with open workspaces and dedicated areas for team meetings and brainstorming sessions.
Technical Infrastructure: The office is equipped with state-of-the-art technology, including high-speed internet, multiple monitors, and testing devices, to support the team's technical support and troubleshooting efforts.
Cross-Functional Collaboration: The technical support team works closely with other departments, such as product management, engineering, and sales, to ensure customer satisfaction and drive product improvement. This cross-functional collaboration is facilitated by the office's open workspace design and dedicated meeting areas.

Work Schedule: The hybrid work schedule for this role is 3 days on-site and 2 days remote, with the on-site schedule from 12:00 pm ET to 9:00 pm ET, including a 1-hour lunch break. The remote work schedule is flexible, with a focus on delivering results and maintaining customer satisfaction.

📝 Enhancement Note: The Progress office in Belen, Costa Rica, provides a modern, collaborative workspace designed to support the technical support team's efforts to deliver exceptional customer support and drive product improvement. The hybrid work schedule offers flexibility while maintaining a strong focus on customer satisfaction and team collaboration.

📄 Application & Technical Interview Process

Interview Process:

Phone Screen: A brief phone call to assess the candidate's communication skills, technical background, and cultural fit.
Technical Assessment: A hands-on technical assessment, focusing on the candidate's ability to troubleshoot complex technical issues, analyze logs, and provide effective solutions.
Behavioral Interview: A structured interview focusing on the candidate's problem-solving skills, leadership experience, and cultural fit.
Final Interview: A final interview with the hiring manager and other key stakeholders to assess the candidate's fit for the role and the team.

Portfolio Review Tips:

Case Studies: Prepare detailed case studies demonstrating your ability to analyze complex technical issues and provide effective solutions. Highlight your problem-solving skills, attention to detail, and customer-centric approach.
Mentoring & Leadership: Prepare examples of your mentoring and leadership skills, such as training materials, team performance improvement initiatives, or customer success stories.
Technical Documentation: Prepare examples of your technical documentation, such as knowledge base articles or user guides, demonstrating your ability to create and maintain accurate, up-to-date information.

Technical Challenge Preparation:

Troubleshooting Scenarios: Familiarize yourself with common technical support and troubleshooting scenarios, and practice your problem-solving skills and attention to detail.
Log Analysis: Brush up on your log analysis skills, and practice analyzing complex logs to identify and resolve technical issues.
Communication Skills: Prepare for questions about your communication skills, and practice explaining technical concepts clearly and concisely.

ATS Keywords: [List of relevant technical support, troubleshooting, and customer success keywords, organized by category]

📝 Enhancement Note: The interview process for the Lead Technical Support Engineer role is designed to assess the candidate's technical expertise, problem-solving skills, leadership experience, and cultural fit. Candidates should prepare thoroughly for each stage of the interview process, emphasizing their technical support and troubleshooting skills, as well as their ability to lead and mentor junior team members.

🛠 Technology Stack & Web Infrastructure

Troubleshooting Tools:

Progress' product suite, including Telerik, Kendo UI, and Sitefinity.
Windows Server roles and features, including IIS, AD, DNS, and file servers.
Networking tools, such as Wireshark, PingPlotter, and SolarWinds.
Database management tools, such as SQL Server Management Studio (SSMS) and MySQL Workbench.
API testing tools, such as Postman and SoapUI.
Log analysis tools, such as ELK Stack, Splunk, or Datadog.

Collaboration & Productivity Tools:

Microsoft Office suite, including Outlook, Excel, PowerPoint, and Word.
Customer Relationship Management (CRM) systems, such as Salesforce, HubSpot, or Zoho CRM.
Project management tools, such as Jira, Asana, or Trello.
Collaboration platforms, such as Microsoft Teams, Slack, or Google Workspace.

📝 Enhancement Note: The technology stack for the Lead Technical Support Engineer role is designed to support the team's troubleshooting and customer support efforts, with a focus on Progress' product suite and relevant technical tools. Candidates should be proficient in using these tools and have a strong technical background in networking, server administration, and database management.

👥 Team Culture & Values

Technical Support Values:

Customer Focus: Progress prioritizes customer success and delivers a world-class customer experience through exceptional technical support and troubleshooting.
Problem-Solving: The technical support team is committed to analyzing complex technical issues and providing effective, efficient solutions.
Continuous Improvement: Progress fosters a culture of continuous improvement, with a focus on iterative development, customer feedback, and data-driven decision-making.
Collaboration: The technical support team works closely with internal stakeholders, such as product management, engineering, and sales, to ensure customer satisfaction and drive product improvement.
Mentorship & Knowledge Sharing: The technical support team values mentorship and knowledge sharing, with a focus on developing junior team members and driving team performance.

Collaboration Style:

Cross-Functional Integration: The technical support team works closely with other departments, such as product management, engineering, and sales, to ensure customer satisfaction and drive product improvement.
Code Review Culture: The technical support team follows a code review culture, with a focus on quality, accuracy, and continuous improvement.
Knowledge Sharing: The technical support team encourages knowledge sharing and collaboration, with a focus on developing junior team members and driving team performance.

📝 Enhancement Note: Progress fosters a customer-centric, collaborative culture with a strong focus on technical expertise, problem-solving, and continuous improvement. The technical support team values mentorship, knowledge sharing, and cross-functional collaboration to ensure customer satisfaction and drive product improvement.

⚡ Challenges & Growth Opportunities

Technical Challenges:

Complex Troubleshooting: The Lead Technical Support Engineer must be able to analyze complex technical issues and provide effective, efficient solutions in a fast-paced, changing environment.
Customer Escalations: The Lead Technical Support Engineer must be able to manage customer escalations, de-escalate potential issues, and maintain customer satisfaction.
Team Leadership: The Lead Technical Support Engineer must be able to mentor and train junior team members, drive team performance, and contribute to the team's knowledge base and best practices.
Product Evolution: The Lead Technical Support Engineer must be able to adapt to changes in Progress' product suite and maintain a deep understanding of the company's products and their integration into customer environments.

Learning & Development Opportunities:

Technical Training: Progress offers ongoing technical training and development opportunities to help the Lead Technical Support Engineer stay up-to-date with the latest technologies and best practices.
Conferences & Events: Progress encourages the Lead Technical Support Engineer to attend industry conferences and events to expand their knowledge and network with other technical professionals.
Mentorship & Leadership Development: Progress provides opportunities for the Lead Technical Support Engineer to develop their mentorship and leadership skills through training, coaching, and on-the-job experiences.

📝 Enhancement Note: The Lead Technical Support Engineer role presents significant technical challenges and growth opportunities, with a strong focus on complex troubleshooting, customer satisfaction, and team leadership. Candidates with a proven track record of success in leading teams to deliver exceptional customer support and a strong technical background in networking, server administration, and database management are well-positioned to succeed in this role and drive team performance.

💡 Interview Preparation

Technical Questions:

Troubleshooting Scenarios: Be prepared to discuss your experience with complex troubleshooting scenarios, and practice explaining your problem-solving approach and attention to detail.
Log Analysis: Brush up on your log analysis skills, and practice analyzing complex logs to identify and resolve technical issues.
Customer Escalations: Prepare for questions about managing customer escalations, de-escalating potential issues, and maintaining customer satisfaction.
Team Leadership: Be ready to discuss your experience with mentoring and training junior team members, driving team performance, and contributing to the team's knowledge base and best practices.

Company & Culture Questions:

Product Knowledge: Research Progress' product suite, and be prepared to discuss your understanding of the company's products and their integration into customer environments.
Industry Trends: Stay up-to-date with the latest trends in technical support and customer success, and be prepared to discuss how you would apply these trends to drive customer satisfaction and product improvement.
Customer-Centric Approach: Prepare to discuss your experience with a customer-centric approach to technical support and troubleshooting, and how you would apply this approach to drive customer satisfaction and product improvement.

Portfolio Presentation Strategy:

Case Studies: Prepare detailed case studies demonstrating your ability to analyze complex technical issues and provide effective solutions. Highlight your problem-solving skills, attention to detail, and customer-centric approach.
Mentoring & Leadership: Prepare examples of your mentoring and leadership skills, such as training materials, team performance improvement initiatives, or customer success stories.
Technical Documentation: Prepare examples of your technical documentation, such as knowledge base articles or user guides, demonstrating your ability to create and maintain accurate, up-to-date information.

📝 Enhancement Note: The interview process for the Lead Technical Support Engineer role is designed to assess the candidate's technical expertise, problem-solving skills, leadership experience, and cultural fit. Candidates should prepare thoroughly for each stage of the interview process, emphasizing their technical support and troubleshooting skills, as well as their ability to lead and mentor junior team members.

📌 Application Steps

To apply for this Lead Technical Support Engineer position:

Update Your Resume: Tailor your resume to highlight your technical support and troubleshooting experience, leadership skills, and relevant technical skills.
Prepare Your Portfolio: Curate a portfolio showcasing your technical support and troubleshooting projects, mentoring and leadership initiatives, and technical documentation.
Research the Company: Familiarize yourself with Progress' product suite, industry trends, and customer-centric approach to technical support and troubleshooting.
Prepare for the Interview: Review the interview process, practice your problem-solving skills, and prepare for questions about your technical expertise, leadership experience, and cultural fit.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and web development/server administration industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.

Lead Technical Support Engineer