The salary range for this role is negotiable, the range being $5,000 - $7,500 USD gross per month. 

About Sezzle:

With a mission to financially empower the next generation, Sezzle is revolutionizing the shopping experience beyond payments, blending cutting-edge tech with seamless, interest-free installment plans that make shopping smarter and more accessible. We’re not just transforming payments; we’re redefining how people discover, interact with, and purchase the things they love while driving real impact on merchant sales through increased conversions and higher order values. As we continue to shape the future of fintech and retail, we’re building an innovative, dynamic team passionate about creating more than just a transaction but a truly unique shopping journey. If you’re excited about pushing boundaries in tech and delivering a game-changing experience for consumers and merchants alike, come join us at Sezzle and help create the future of shopping!

About the Role: 

We are seeking a detail-oriented and proactive IT Vendor Management Program Manager to lead the execution of our third-party risk management framework. This role is the backbone of our vendor oversight, ensuring that every partnership—from non-critical services to complex bank integrations—aligns with our high standards for security, compliance, and operational excellence. You will have the authority to manage the vendor lifecycle and ensure our program remains robust under regulatory scrutiny.

Compensation

The compensation range for the role is $5,000 - $7,500 USD GROSS per month as a contractor. Specific compensation offered to a candidate may be dependent on factors such as education, experience, qualifications, and alignment with market data. Exceptional candidates may receive salaries outside of the posted ranges.

What You'll Do:

• Standards & Governance: work cross-functionally with IT, Legal, and Compliance teams to establish and maintain third-party risk standards and governance practices.
• Due Diligence & Monitoring: Conduct comprehensive vendor due diligence and ongoing monitoring activities, including evaluating consumer-impact risk, complaint analysis, and confirming privacy and data protection standards.
• Documentation & Reporting: Manage third-party risk documentation and reporting, including maintaining the vendor and data processor inventory, ensuring timely onboarding and offboarding due diligence, and executing periodic compliance reviews.
• Risk Assessment: Execute day-to-day risk assessments to determine vendor criticality and identify inherent risks in categories such as PII handling, BSA/AML, and credit decisioning.
• Collaboration: Work cross-functionally with Legal to ensure effective contracts are in place and with Information Security to validate the technical safeguards of our third-party partners.
• Issue Escalation: Identify, track, and escalate risk events or performance failures to senior leadership and bank partners through established issue-tracking systems.

What We Look For:

• Experience: 7+ years of professional experience in vendor risk management, procurement, or third-party compliance, preferably within the fintech or regulated financial services industry.
• Regulatory Knowledge: Understanding of third-party risk management lifecycle and regulatory guidance (e.g., PCI-DSS, SOC 2, GLBA, and BSA/AML).
• Execution: Proven track record of managing a high volume of vendor assessments and maintaining a state of "audit-readiness" for bank partners and regulators.
• Education: Bachelor’s degree in Business, Finance, Law, or equivalent practical experience.

About You: 

• You have relentlessly high standards - many people may think your standards are unreasonably high. You are continually raising the bar and driving those around you to deliver great results. You make sure that defects do not get sent down the line and that problems are fixed so they stay fixed.
• You’re not bound by convention - your success—and much of the fun—lies in developing new ways to do things
• You need action - speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking.
• You earn trust - you listen attentively, speak candidly, and treat others respectfully.
• You have backbone; disagree, then commit - you can respectfully challenge decisions when you disagree, even when doing so is uncomfortable or exhausting. You have conviction and are tenacious. You do not compromise for the sake of social cohesion. Once a decision is determined, you commit wholly.

What Makes Working at Sezzle Awesome? 

At Sezzle, we are more than just brilliant engineers, passionate data enthusiasts, out-of-the-box thinkers, and determined innovators. We believe in surrounding ourselves with only the best and the brightest individuals. Our culture is not defined by a certain set of perks designed to give the illusion of the traditional startup culture, but rather, it is the visible example living in every employee that we hire. 

#Li-remote #full-time

The salary range for this role is negotiable, the range being $5,000 - $7,500 USD gross per month. 

About Sezzle:

With a mission to financially empower the next generation, Sezzle is revolutionizing the shopping experience beyond payments, blending cutting-edge tech with seamless, interest-free installment plans that make shopping smarter and more accessible. We’re not just transforming payments; we’re redefining how people discover, interact with, and purchase the things they love while driving real impact on merchant sales through increased conversions and higher order values. As we continue to shape the future of fintech and retail, we’re building an innovative, dynamic team passionate about creating more than just a transaction but a truly unique shopping journey. If you’re excited about pushing boundaries in tech and delivering a game-changing experience for consumers and merchants alike, come join us at Sezzle and help create the future of shopping!

About the Role: 

We are seeking a detail-oriented and proactive IT Vendor Management Program Manager to lead the execution of our third-party risk management framework. This role is the backbone of our vendor oversight, ensuring that every partnership—from non-critical services to complex bank integrations—aligns with our high standards for security, compliance, and operational excellence. You will have the authority to manage the vendor lifecycle and ensure our program remains robust under regulatory scrutiny.

Compensation

The compensation range for the role is $5,000 - $7,500 USD GROSS per month as a contractor. Specific compensation offered to a candidate may be dependent on factors such as education, experience, qualifications, and alignment with market data. Exceptional candidates may receive salaries outside of the posted ranges.

What You'll Do:

• Standards & Governance: work cross-functionally with IT, Legal, and Compliance teams to establish and maintain third-party risk standards and governance practices.
• Due Diligence & Monitoring: Conduct comprehensive vendor due diligence and ongoing monitoring activities, including evaluating consumer-impact risk, complaint analysis, and confirming privacy and data protection standards.
• Documentation & Reporting: Manage third-party risk documentation and reporting, including maintaining the vendor and data processor inventory, ensuring timely onboarding and offboarding due diligence, and executing periodic compliance reviews.
• Risk Assessment: Execute day-to-day risk assessments to determine vendor criticality and identify inherent risks in categories such as PII handling, BSA/AML, and credit decisioning.
• Collaboration: Work cross-functionally with Legal to ensure effective contracts are in place and with Information Security to validate the technical safeguards of our third-party partners.
• Issue Escalation: Identify, track, and escalate risk events or performance failures to senior leadership and bank partners through established issue-tracking systems.

What We Look For:

• Experience: 7+ years of professional experience in vendor risk management, procurement, or third-party compliance, preferably within the fintech or regulated financial services industry.
• Regulatory Knowledge: Understanding of third-party risk management lifecycle and regulatory guidance (e.g., PCI-DSS, SOC 2, GLBA, and BSA/AML).
• Execution: Proven track record of managing a high volume of vendor assessments and maintaining a state of "audit-readiness" for bank partners and regulators.
• Education: Bachelor’s degree in Business, Finance, Law, or equivalent practical experience.

About You: 

• You have relentlessly high standards - many people may think your standards are unreasonably high. You are continually raising the bar and driving those around you to deliver great results. You make sure that defects do not get sent down the line and that problems are fixed so they stay fixed.
• You’re not bound by convention - your success—and much of the fun—lies in developing new ways to do things
• You need action - speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking.
• You earn trust - you listen attentively, speak candidly, and treat others respectfully.
• You have backbone; disagree, then commit - you can respectfully challenge decisions when you disagree, even when doing so is uncomfortable or exhausting. You have conviction and are tenacious. You do not compromise for the sake of social cohesion. Once a decision is determined, you commit wholly.

What Makes Working at Sezzle Awesome? 

At Sezzle, we are more than just brilliant engineers, passionate data enthusiasts, out-of-the-box thinkers, and determined innovators. We believe in surrounding ourselves with only the best and the brightest individuals. Our culture is not defined by a certain set of perks designed to give the illusion of the traditional startup culture, but rather, it is the visible example living in every employee that we hire. 

#Li-remote #full-time

The salary range for this role is negotiable, the range being $5,000 - $7,500 USD gross per month. 

About Sezzle:

With a mission to financially empower the next generation, Sezzle is revolutionizing the shopping experience beyond payments, blending cutting-edge tech with seamless, interest-free installment plans that make shopping smarter and more accessible. We’re not just transforming payments; we’re redefining how people discover, interact with, and purchase the things they love while driving real impact on merchant sales through increased conversions and higher order values. As we continue to shape the future of fintech and retail, we’re building an innovative, dynamic team passionate about creating more than just a transaction but a truly unique shopping journey. If you’re excited about pushing boundaries in tech and delivering a game-changing experience for consumers and merchants alike, come join us at Sezzle and help create the future of shopping!

About the Role: 

We are seeking a detail-oriented and proactive IT Vendor Management Program Manager to lead the execution of our third-party risk management framework. This role is the backbone of our vendor oversight, ensuring that every partnership—from non-critical services to complex bank integrations—aligns with our high standards for security, compliance, and operational excellence. You will have the authority to manage the vendor lifecycle and ensure our program remains robust under regulatory scrutiny.

Compensation

The compensation range for the role is $5,000 - $7,500 USD GROSS per month as a contractor. Specific compensation offered to a candidate may be dependent on factors such as education, experience, qualifications, and alignment with market data. Exceptional candidates may receive salaries outside of the posted ranges.

What You'll Do:

• Standards & Governance: work cross-functionally with IT, Legal, and Compliance teams to establish and maintain third-party risk standards and governance practices.
• Due Diligence & Monitoring: Conduct comprehensive vendor due diligence and ongoing monitoring activities, including evaluating consumer-impact risk, complaint analysis, and confirming privacy and data protection standards.
• Documentation & Reporting: Manage third-party risk documentation and reporting, including maintaining the vendor and data processor inventory, ensuring timely onboarding and offboarding due diligence, and executing periodic compliance reviews.
• Risk Assessment: Execute day-to-day risk assessments to determine vendor criticality and identify inherent risks in categories such as PII handling, BSA/AML, and credit decisioning.
• Collaboration: Work cross-functionally with Legal to ensure effective contracts are in place and with Information Security to validate the technical safeguards of our third-party partners.
• Issue Escalation: Identify, track, and escalate risk events or performance failures to senior leadership and bank partners through established issue-tracking systems.

What We Look For:

• Experience: 7+ years of professional experience in vendor risk management, procurement, or third-party compliance, preferably within the fintech or regulated financial services industry.
• Regulatory Knowledge: Understanding of third-party risk management lifecycle and regulatory guidance (e.g., PCI-DSS, SOC 2, GLBA, and BSA/AML).
• Execution: Proven track record of managing a high volume of vendor assessments and maintaining a state of "audit-readiness" for bank partners and regulators.
• Education: Bachelor’s degree in Business, Finance, Law, or equivalent practical experience.

About You: 

• You have relentlessly high standards - many people may think your standards are unreasonably high. You are continually raising the bar and driving those around you to deliver great results. You make sure that defects do not get sent down the line and that problems are fixed so they stay fixed.
• You’re not bound by convention - your success—and much of the fun—lies in developing new ways to do things
• You need action - speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking.
• You earn trust - you listen attentively, speak candidly, and treat others respectfully.
• You have backbone; disagree, then commit - you can respectfully challenge decisions when you disagree, even when doing so is uncomfortable or exhausting. You have conviction and are tenacious. You do not compromise for the sake of social cohesion. Once a decision is determined, you commit wholly.

What Makes Working at Sezzle Awesome? 

At Sezzle, we are more than just brilliant engineers, passionate data enthusiasts, out-of-the-box thinkers, and determined innovators. We believe in surrounding ourselves with only the best and the brightest individuals. Our culture is not defined by a certain set of perks designed to give the illusion of the traditional startup culture, but rather, it is the visible example living in every employee that we hire. 

#Li-remote #full-time

The salary range for this role is negotiable, the range being $5,000 - $7,500 USD gross per month. 

About Sezzle:

With a mission to financially empower the next generation, Sezzle is revolutionizing the shopping experience beyond payments, blending cutting-edge tech with seamless, interest-free installment plans that make shopping smarter and more accessible. We’re not just transforming payments; we’re redefining how people discover, interact with, and purchase the things they love while driving real impact on merchant sales through increased conversions and higher order values. As we continue to shape the future of fintech and retail, we’re building an innovative, dynamic team passionate about creating more than just a transaction but a truly unique shopping journey. If you’re excited about pushing boundaries in tech and delivering a game-changing experience for consumers and merchants alike, come join us at Sezzle and help create the future of shopping!

About the Role: 

We are seeking a detail-oriented and proactive IT Vendor Management Program Manager to lead the execution of our third-party risk management framework. This role is the backbone of our vendor oversight, ensuring that every partnership—from non-critical services to complex bank integrations—aligns with our high standards for security, compliance, and operational excellence. You will have the authority to manage the vendor lifecycle and ensure our program remains robust under regulatory scrutiny.

Compensation

The compensation range for the role is $5,000 - $7,500 USD GROSS per month as a contractor. Specific compensation offered to a candidate may be dependent on factors such as education, experience, qualifications, and alignment with market data. Exceptional candidates may receive salaries outside of the posted ranges.

What You'll Do:

• Standards & Governance: work cross-functionally with IT, Legal, and Compliance teams to establish and maintain third-party risk standards and governance practices.
• Due Diligence & Monitoring: Conduct comprehensive vendor due diligence and ongoing monitoring activities, including evaluating consumer-impact risk, complaint analysis, and confirming privacy and data protection standards.
• Documentation & Reporting: Manage third-party risk documentation and reporting, including maintaining the vendor and data processor inventory, ensuring timely onboarding and offboarding due diligence, and executing periodic compliance reviews.
• Risk Assessment: Execute day-to-day risk assessments to determine vendor criticality and identify inherent risks in categories such as PII handling, BSA/AML, and credit decisioning.
• Collaboration: Work cross-functionally with Legal to ensure effective contracts are in place and with Information Security to validate the technical safeguards of our third-party partners.
• Issue Escalation: Identify, track, and escalate risk events or performance failures to senior leadership and bank partners through established issue-tracking systems.

What We Look For:

• Experience: 7+ years of professional experience in vendor risk management, procurement, or third-party compliance, preferably within the fintech or regulated financial services industry.
• Regulatory Knowledge: Understanding of third-party risk management lifecycle and regulatory guidance (e.g., PCI-DSS, SOC 2, GLBA, and BSA/AML).
• Execution: Proven track record of managing a high volume of vendor assessments and maintaining a state of "audit-readiness" for bank partners and regulators.
• Education: Bachelor’s degree in Business, Finance, Law, or equivalent practical experience.

About You: 

• You have relentlessly high standards - many people may think your standards are unreasonably high. You are continually raising the bar and driving those around you to deliver great results. You make sure that defects do not get sent down the line and that problems are fixed so they stay fixed.
• You’re not bound by convention - your success—and much of the fun—lies in developing new ways to do things
• You need action - speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking.
• You earn trust - you listen attentively, speak candidly, and treat others respectfully.
• You have backbone; disagree, then commit - you can respectfully challenge decisions when you disagree, even when doing so is uncomfortable or exhausting. You have conviction and are tenacious. You do not compromise for the sake of social cohesion. Once a decision is determined, you commit wholly.

What Makes Working at Sezzle Awesome? 

At Sezzle, we are more than just brilliant engineers, passionate data enthusiasts, out-of-the-box thinkers, and determined innovators. We believe in surrounding ourselves with only the best and the brightest individuals. Our culture is not defined by a certain set of perks designed to give the illusion of the traditional startup culture, but rather, it is the visible example living in every employee that we hire. 

#Li-remote #full-time

The salary range for this role is negotiable, the range being $5,000 - $7,500 USD gross per month. 

About Sezzle:

With a mission to financially empower the next generation, Sezzle is revolutionizing the shopping experience beyond payments, blending cutting-edge tech with seamless, interest-free installment plans that make shopping smarter and more accessible. We’re not just transforming payments; we’re redefining how people discover, interact with, and purchase the things they love while driving real impact on merchant sales through increased conversions and higher order values. As we continue to shape the future of fintech and retail, we’re building an innovative, dynamic team passionate about creating more than just a transaction but a truly unique shopping journey. If you’re excited about pushing boundaries in tech and delivering a game-changing experience for consumers and merchants alike, come join us at Sezzle and help create the future of shopping!

About the Role: 

We are seeking a detail-oriented and proactive IT Vendor Management Program Manager to lead the execution of our third-party risk management framework. This role is the backbone of our vendor oversight, ensuring that every partnership—from non-critical services to complex bank integrations—aligns with our high standards for security, compliance, and operational excellence. You will have the authority to manage the vendor lifecycle and ensure our program remains robust under regulatory scrutiny.

Compensation

The compensation range for the role is $5,000 - $7,500 USD GROSS per month as a contractor. Specific compensation offered to a candidate may be dependent on factors such as education, experience, qualifications, and alignment with market data. Exceptional candidates may receive salaries outside of the posted ranges.

What You'll Do:

• Standards & Governance: work cross-functionally with IT, Legal, and Compliance teams to establish and maintain third-party risk standards and governance practices.
• Due Diligence & Monitoring: Conduct comprehensive vendor due diligence and ongoing monitoring activities, including evaluating consumer-impact risk, complaint analysis, and confirming privacy and data protection standards.
• Documentation & Reporting: Manage third-party risk documentation and reporting, including maintaining the vendor and data processor inventory, ensuring timely onboarding and offboarding due diligence, and executing periodic compliance reviews.
• Risk Assessment: Execute day-to-day risk assessments to determine vendor criticality and identify inherent risks in categories such as PII handling, BSA/AML, and credit decisioning.
• Collaboration: Work cross-functionally with Legal to ensure effective contracts are in place and with Information Security to validate the technical safeguards of our third-party partners.
• Issue Escalation: Identify, track, and escalate risk events or performance failures to senior leadership and bank partners through established issue-tracking systems.

What We Look For:

• Experience: 7+ years of professional experience in vendor risk management, procurement, or third-party compliance, preferably within the fintech or regulated financial services industry.
• Regulatory Knowledge: Understanding of third-party risk management lifecycle and regulatory guidance (e.g., PCI-DSS, SOC 2, GLBA, and BSA/AML).
• Execution: Proven track record of managing a high volume of vendor assessments and maintaining a state of "audit-readiness" for bank partners and regulators.
• Education: Bachelor’s degree in Business, Finance, Law, or equivalent practical experience.

About You: 

• You have relentlessly high standards - many people may think your standards are unreasonably high. You are continually raising the bar and driving those around you to deliver great results. You make sure that defects do not get sent down the line and that problems are fixed so they stay fixed.
• You’re not bound by convention - your success—and much of the fun—lies in developing new ways to do things
• You need action - speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking.
• You earn trust - you listen attentively, speak candidly, and treat others respectfully.
• You have backbone; disagree, then commit - you can respectfully challenge decisions when you disagree, even when doing so is uncomfortable or exhausting. You have conviction and are tenacious. You do not compromise for the sake of social cohesion. Once a decision is determined, you commit wholly.

What Makes Working at Sezzle Awesome? 

At Sezzle, we are more than just brilliant engineers, passionate data enthusiasts, out-of-the-box thinkers, and determined innovators. We believe in surrounding ourselves with only the best and the brightest individuals. Our culture is not defined by a certain set of perks designed to give the illusion of the traditional startup culture, but rather, it is the visible example living in every employee that we hire. 

#Li-remote #full-time

The salary range for this role is negotiable, the range being $5,000 - $7,500 USD gross per month. 

About Sezzle:

With a mission to financially empower the next generation, Sezzle is revolutionizing the shopping experience beyond payments, blending cutting-edge tech with seamless, interest-free installment plans that make shopping smarter and more accessible. We’re not just transforming payments; we’re redefining how people discover, interact with, and purchase the things they love while driving real impact on merchant sales through increased conversions and higher order values. As we continue to shape the future of fintech and retail, we’re building an innovative, dynamic team passionate about creating more than just a transaction but a truly unique shopping journey. If you’re excited about pushing boundaries in tech and delivering a game-changing experience for consumers and merchants alike, come join us at Sezzle and help create the future of shopping!

About the Role: 

We are seeking a detail-oriented and proactive IT Vendor Management Program Manager to lead the execution of our third-party risk management framework. This role is the backbone of our vendor oversight, ensuring that every partnership—from non-critical services to complex bank integrations—aligns with our high standards for security, compliance, and operational excellence. You will have the authority to manage the vendor lifecycle and ensure our program remains robust under regulatory scrutiny.

Compensation

The compensation range for the role is $5,000 - $7,500 USD GROSS per month as a contractor. Specific compensation offered to a candidate may be dependent on factors such as education, experience, qualifications, and alignment with market data. Exceptional candidates may receive salaries outside of the posted ranges.

What You'll Do:

• Standards & Governance: work cross-functionally with IT, Legal, and Compliance teams to establish and maintain third-party risk standards and governance practices.
• Due Diligence & Monitoring: Conduct comprehensive vendor due diligence and ongoing monitoring activities, including evaluating consumer-impact risk, complaint analysis, and confirming privacy and data protection standards.
• Documentation & Reporting: Manage third-party risk documentation and reporting, including maintaining the vendor and data processor inventory, ensuring timely onboarding and offboarding due diligence, and executing periodic compliance reviews.
• Risk Assessment: Execute day-to-day risk assessments to determine vendor criticality and identify inherent risks in categories such as PII handling, BSA/AML, and credit decisioning.
• Collaboration: Work cross-functionally with Legal to ensure effective contracts are in place and with Information Security to validate the technical safeguards of our third-party partners.
• Issue Escalation: Identify, track, and escalate risk events or performance failures to senior leadership and bank partners through established issue-tracking systems.

What We Look For:

• Experience: 7+ years of professional experience in vendor risk management, procurement, or third-party compliance, preferably within the fintech or regulated financial services industry.
• Regulatory Knowledge: Understanding of third-party risk management lifecycle and regulatory guidance (e.g., PCI-DSS, SOC 2, GLBA, and BSA/AML).
• Execution: Proven track record of managing a high volume of vendor assessments and maintaining a state of "audit-readiness" for bank partners and regulators.
• Education: Bachelor’s degree in Business, Finance, Law, or equivalent practical experience.

About You: 

• You have relentlessly high standards - many people may think your standards are unreasonably high. You are continually raising the bar and driving those around you to deliver great results. You make sure that defects do not get sent down the line and that problems are fixed so they stay fixed.
• You’re not bound by convention - your success—and much of the fun—lies in developing new ways to do things
• You need action - speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking.
• You earn trust - you listen attentively, speak candidly, and treat others respectfully.
• You have backbone; disagree, then commit - you can respectfully challenge decisions when you disagree, even when doing so is uncomfortable or exhausting. You have conviction and are tenacious. You do not compromise for the sake of social cohesion. Once a decision is determined, you commit wholly.

What Makes Working at Sezzle Awesome? 

At Sezzle, we are more than just brilliant engineers, passionate data enthusiasts, out-of-the-box thinkers, and determined innovators. We believe in surrounding ourselves with only the best and the brightest individuals. Our culture is not defined by a certain set of perks designed to give the illusion of the traditional startup culture, but rather, it is the visible example living in every employee that we hire. 

#Li-remote #full-time

Title: IT Operations Analyst

Location: Bogota, hybrid

Hiring Manager: Dave Bergen

About Sezzle:

With a mission to financially empower the next generation, Sezzle is revolutionizing the shopping experience beyond payments, blending cutting-edge tech with seamless, interest-free installment plans that make shopping smarter and more accessible. We’re not just transforming payments; we’re redefining how people discover, interact with, and purchase the things they love while driving real impact on merchant sales through increased conversions and higher order values. As we continue to shape the future of fintech and retail, we’re building an innovative, dynamic team passionate about creating more than just a transaction but a truly unique shopping journey. If you’re excited about pushing boundaries in tech and delivering a game-changing experience for consumers and merchants alike, come join us at Sezzle and help create the future of shopping!

About the Role: 

As a Sezzle IT Operations Analyst, you will be an integral part of the IT Operations team as we continue to grow our presence in Colombia. As Colombia's IT Operations point of contact, you will be accountable for local device inventory management, Google Workspace administration, MDM implementation, and ongoing maintenance. Most importantly, you will provide our end users the highest level of IT Support.

Compensation

The compensation range for the role is $1,500 - $2,000 USD GROSS per month as a contractor. Specific compensation offered to a candidate may be dependent on factors such as education, experience, qualifications, and alignment with market data. Exceptional candidates may receive salaries outside of the posted ranges.

What You'll Do:

• Be the one of the main points of contact for device inventory procurement, deployment, physical security, and management for employees in Colombia, including macOS and Windows OS-based devices.
• Respond promptly to incoming ITSD tickets in Jira, working on the issue from inception to completion.
• Contribute to working down assigned items in our existing Jira backlog of initiative-based elements as we work to continue to be a more proactive IT Operations team.
• Maintain a high level of technical change awareness regarding our large application stack and be well-versed in IT Security. You should possess the ability and confidence to convey this information accurately to the larger engineering team and, in some cases, the organization as a whole.
• Obtain and provision hardware and software requests as assigned. This position requires on-call responsibilities and occasional after-hours work.
• Conduct IT Operations onboarding training for organization new hires, as well as processing IT-focused employee termination responsibilities
• Contribute to existing and future IT audit work on access control history and quarterly software vendor audits.

What We Look For:

• Applicants must be fluent in English.
• Due to the nature of this role, candidates must be based in Bogota, Colombia, and able to work both remotely and in-office when required.
• Experience: 2 -6 years
• Has a team-oriented mindset, sharing the workload but also being willing to step up when resources are minimized. Our ideal candidate is an excellent communicator who shows patience and a willingness to learn. 
• Systems and skills knowledge should include a high aptitude in cloud-based productivity suite administration, macOS device management and configuration using enterprise tools, IT service management platforms with experience in ticket automation and workflow design, enterprise Windows device management using third-party solutions, productivity software suite administration, and management of enterprise endpoint security platforms.

Preferred Knowledge and Skills:

• Possess the ability to be a self-starter:  
  • Identify a problem.
  • Assess the situation and any variables
  • Work quickly and accurately to resolve the problem
  • Identify areas where processes can be improved to reduce the reoccurrence of existing problems
  • Take the initiative and work autonomously to implement the improvement.
• Ability to react to a rapidly changing organization with a true start-up mentality.
• Experience and comfort working on an agile team – an ideal candidate should be familiar with agile concepts, including Jira ticketing classification, pointing, and meeting workflows.
• Possess a high level of organization with the ability to document workflows accurately and in a manner that can be replicated. Change management is critical to the success of our IT Operations team for both auditing purposes and process improvement. Our ideal candidate would have experience and comfort in bringing these skills to Sezzle.
• Experience working with PCI-DSS, SOC 2 Type 2,  and CIS controls; specifically in implementation, documentation, administration, and continued adherence to these controls.

About You: 

• A+ character. We are team-first here at Sezzle. 
• A hard-working mentality. It’s early and there is still a lot to build. 
• An excellent communicator. 
• Ownership. You aren’t afraid to take on new responsibilities and you act like an owner in everything you do.
• A fun attitude. Life’s too short. We can have fun while we work hard on cool things. 
• Smarts. We need people that are smart enough to make decisions on their own and also smart enough to know when they need input from others. 

What Makes Working at Sezzle Awesome? 

At Sezzle, we are more than just brilliant engineers, passionate data enthusiasts, out-of-the-box thinkers, and determined innovators. We believe in surrounding ourselves with only the best and the brightest individuals. Our culture is not defined by a certain set of perks designed to give the illusion of the traditional startup culture, but rather, it is the visible example living in every employee that we hire. 

Equal Employment Opportunity: Sezzle Inc. is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate based on race, color, religion, sex, national origin, age, disability, genetic information, pregnancy, or any other legally protected status. Sezzle recognizes and values the importance of diversity and inclusion in enriching the employment experience of its employees and in supporting our mission.

#LI-Onsite #Full-time

Robots & Pencils is seeking an experienced, outcome-oriented IT Manager to lead and evolve our internal technology environment across a distributed, international team. 

You will own the lifecycle, performance, and reliability of internal systems supporting team members across four countries, with offices in Cleveland, Calgary, Lviv (Ukraine), and Bogota 

You will implement scalable systems, standardize core processes, and strengthen internal technology foundations so our teams can move faster, collaborate better, and focus on meaningful client outcomes. 

Key Responsibilities 

Application Lifecycle & Systems Ownership 

• Own application lifecycle management end-to-end, including evaluation, acquisition, rollout, support, maintenance, optimization, and retirement 

• Rationalize underused or redundant tools to reduce platform sprawl 

• Lead critical systems implementations, including HRIS and PSA platforms 

• Build structured implementation plans with clear milestones, adoption targets, and risk mitigation strategies 

• Ensure internal systems scale with company growth across offices and time zones 

Process Standardization & Operational Excellence 

• Standardize onboarding and offboarding processes across countries and offices 

• Improve helpdesk and service workflows for speed, clarity, and accountability 

• Create repeatable, documented processes that balance consistency with flexibility 

• Strengthen internal operational visibility without introducing unnecessary bureaucracy 

• Continuously refine systems based on usage patterns and team feedback 

Vendor, Inventory & Cost Management 

• Own vendor relationships and service-level agreements 

• Manage hardware and software procurement, inventory tracking, and cost allocation 

• Strengthen oversight of SaaS subscriptions and AI-related spend 

• Optimize licensing and subscription usage for efficiency and scalability 

• Ensure vendor performance meets reliability and support expectations 

Security & Compliance 

• Support security awareness training and internal risk assessments 

• Contribute to annual SOC 2 compliance certification efforts 

• Strengthen documentation and audit readiness, including maintaining a structured Vanta repository 

• Ensure internal systems meet security, governance, and compliance standards 

• Proactively identify and mitigate operational and compliance risks 

Team Leadership & Cross-Functional Collaboration 

• Lead the team responsible for helpdesk support and systems maintenance 

• Partner closely with HR, Operations, and Engineering to translate business needs into durable IT solutions 

• Communicate clearly with both technical and non-technical stakeholders 

• Balance competing priorities with sound judgment and a service-oriented mindset 

• Drive accountability and clarity across distributed teams 

Required Skills & Qualifications 

• 8+ years of relevant corporate IT experience 

• Experience analyzing, implementing, and evaluating enterprise IT systems 

• Strong background in SaaS management and cloud infrastructure (AWS) 

• Demonstrated success with security frameworks, audits, and compliance programs, including SOC 2 

• Fluency with Microsoft 365 (certification is a plus) and comfort working with tools such as GitHub and AWS 

• Project management experience with successful rollouts of new systems and documented risk mitigation strategies 

• English fluency (written and spoken) 

Nice to Have 

• PSA or ERP implementation experience 

• Experience operating in distributed, international organizations 

• Exposure to SaaS rationalization and cost optimization initiatives 

Personal Competencies 

• Outcome-Oriented – Focuses on operational impact, reliability, and measurable improvements. 

• Systems Thinker – Standardizes processes without creating unnecessary friction. 

• Service-Minded – Prioritizes user experience for internal teams. 

• Operationally Disciplined – Drives clarity, structure, and accountability. 

• Adaptable – Balances competing priorities calmly and effectively. 

• Ownership-Driven – Follows through and ensures systems perform as intended. 

Why This Role Matters 

At Robots & Pencils, we build smart systems for the human world. When our internal technology is strong, our teams move faster, collaborate better, and spend more time delivering meaningful outcomes for clients. This role turns IT into a true enabler of creativity, security, and scale across borders and time zones. 

You will strengthen the foundation that allows every product team to operate at a higher level. This is operational leadership with measurable organizational impact. 

Why Join Robots & Pencils? 

We don’t just maintain systems; we build environments where teams can do their best work. 

You’ll help modernize internal infrastructure, lead high-impact system implementations, and influence how a distributed digital product company operates at scale. 

You’ll work at the intersection of operations, security, and systems architecture, driving durable improvements that power the entire organization.