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Digital Insurance Agent Jobs in Calgary, AB (NOW HIRING)

We offer statutory benefits, medical insurance, life insurance, paid time off, learning and growth ... Collaborate on strategic technology integrations across the digital stack with the IT/Architecture ...

Digital Insurance Agent information

What are some common challenges faced by Digital Insurance Agents, and how can they be addressed?

Digital Insurance Agents often face challenges such as adapting to rapidly changing technology platforms, maintaining strong client relationships without in-person meetings, and staying up-to-date with evolving insurance products. To overcome these, agents should invest time in ongoing training, utilize digital communication tools to foster trust with clients, and collaborate closely with their team for knowledge sharing. Proactively engaging with clients through personalized digital interactions and leveraging CRM systems can also help strengthen client loyalty and streamline workflows.

How much do virtual insurance agents make?

Virtual insurance agents typically earn between $40,000 and $70,000 annually, with top performers making over $100,000 through commissions and bonuses. Income depends on experience, sales skills, and the volume of policies sold, often requiring certifications and strong customer service skills.

How can I make 2000 a week working from home?

A Digital Insurance Agent can potentially earn $2,000 or more weekly by building a client base through online marketing, providing excellent service, and earning commissions on policies sold. Success depends on experience, sales skills, and the ability to generate leads remotely, often requiring certifications and familiarity with digital communication tools.

What are the key skills and qualifications needed to thrive as a Digital Insurance Agent, and why are they important?

To thrive as a Digital Insurance Agent, you need a solid understanding of insurance products, sales techniques, and regulatory compliance, often supported by a relevant license. Familiarity with customer relationship management (CRM) software, digital communication platforms, and online quoting tools is typical for the role. Strong interpersonal skills, digital literacy, and the ability to build trust remotely set top performers apart. These skills enable agents to effectively engage clients, streamline processes, and deliver personalized service in a digital-first insurance environment.

What is the highest paying insurance agent job?

The highest paying insurance agent roles are typically those specializing in high-net-worth clients, such as private client or wealth management insurance agents, or those working in executive and corporate insurance. These positions often require advanced certifications, extensive experience, and strong sales skills, with top earners earning six-figure incomes or more through commissions and bonuses.

What is a Digital Insurance Agent?

A Digital Insurance Agent is a licensed professional who sells and manages insurance policies primarily through online platforms and digital communication tools. Unlike traditional agents who rely on face-to-face meetings, digital agents use websites, email, chat, and video calls to interact with clients. Their role involves recommending coverage options, answering customer questions, and streamlining the application and claims process using technology. Digital Insurance Agents often work for insurance companies, digital brokerages, or as independent contractors. Their digital approach makes insurance services more accessible and efficient for clients.

How to make money through digital insurance?

A digital insurance agent makes money by earning commissions on policies sold, such as auto, health, or life insurance, often through online platforms. Success depends on building a client base, understanding insurance products, and utilizing digital marketing tools. Certifications like the General Lines license can enhance credibility and earning potential.

What is the difference between Digital Insurance Agent vs Insurance Broker?

AspectDigital Insurance AgentInsurance Broker
CredentialsMay require insurance licenses, certifications in digital salesLicensed insurance broker, often with broader certifications
Work EnvironmentOnline platforms, digital tools, remote workOffice-based or remote, client meetings, broker offices
Employer & Industry UsageInsurance companies, online agencies, insurtech firmsIndependent or agency-based, multiple insurance providers
Search & Comparison IntentCustomer-focused, digital sales, policy recommendationsClient advocacy, policy comparison across providers

While both roles involve selling insurance policies, a Digital Insurance Agent primarily operates online, leveraging digital tools to reach customers and sell policies. An Insurance Broker acts as an intermediary, offering clients a range of policies from different providers, often through in-person or traditional channels. Understanding these differences helps consumers and professionals choose the right role or service for their needs.

What cities near Calgary, AB are hiring for Digital Insurance Agent jobs? Cities near Calgary, AB with the most Digital Insurance Agent job openings:

PMO Strategic Projects Lead

360training

Calgary, AB • Hybrid

Full-time

Medical, Dental, Life, PTO

Posted 24 days ago


Job description

360training
At 360training, we’re more than an online training provider—we’re on a mission to empower people and organizations to thrive. As a fast-growing leader in online and live training across multiple industries, we deliver regulatory-approved training and certifications that power careers and businesses.
Our culture is grounded in two values: Deliver Results and Do the Right Thing. We operate as a collaborative, performance-driven organization where data plays a critical role in shaping strategy and outcomes. If you’re excited to turn analytics into impact and influence meaningful decisions, 360training is the place for you.
360training offers a compelling compensation package that ties to performance and impact. We offer statutory benefits, medical insurance, life insurance, paid time off, learning and growth opportunities, and a comprehensive employee engagement and wellness program.
PMO Strategic Projects Lead
The PMO Strategic Projects Lead role leads and rolls out the end-to-end orchestration of strategic technology initiatives across our digital ecosystem — our learning management systems (LMS), web and content platforms (Drupal), headless commerce (Medusa), and product information / digital experience management (Pimcore) — along with the integrations and migrations that connect them. This is a hybrid role: part portfolio governance leader, part technically fluent program manager, and part change agent who brings stakeholders together and keeps delivery moving.
The role requires a rare blend of portfolio management expertise, hands-on Agile delivery discipline, applied technical fluency, and AI literacy, paired with the soft skills — stakeholder management, facilitation, and communication — needed to influence without direct authority.
Key Responsibilities
Portfolio Governance amp; Prioritization
  • Own the project intake, prioritization, and approval process, ensuring every initiative maps clearly to strategic objectives and measurable business value.
  • Own structured prioritization frameworks such as RICE (Reach, Impact, Confidence, Effort) and weighted/value-vs-effort scoring to rank competing demands objectively and defensibly.
  • Facilitate portfolio visibility on review boards, steering committees, and quarterly planning ceremonies, framing trade-offs and driving clear go / no-go / re-prioritize decisions.
  • Develop and maintain portfolio dashboards to track delivery health (change requests, MVP, scope, DoD, etc.), risk, cross-platform dependencies, capacity, and benefit realization to provide company visibility.
  • Enforce PMO standards — project charters, stage-gates, RAID logs, definition-of-done, and consistent status reporting — while keeping governance lightweight and value-adding rather than bureaucratic.
  • Partner with resource managers to align capacity and demand management across the portfolio.
Agile Delivery amp; Scaled Frameworks
  • Drive delivery using Agile methodologies and scaled frameworks — SAFe (Scaled Agile Framework) and/or LeSS (Large-Scale Scrum) — coordinating across multiple teams, programs, and Agile Release Trains or iterative releases.
  • Support Lean Portfolio Management practices: align strategic themes to epics, manage portfolio Kanban / intake flow, and enable agile, incremental funding rather than fixed annual budgets.
  • Coordinate cross-team planning, dependency mapping, and synchronization so initiatives spanning LMS, Credit Reporting, Drupal, Medusa, Pimcore, etc., stay aligned.
  • Remove cross-program impediments, manage risks and dependencies proactively, and protect delivery cadence and flow. Champion continuous improvement through retrospectives, flow metrics, and data-informed adjustments to ways of working.
Technology Programs: Platforms, Integrations amp; Migrations
  • Collaborate on strategic technology integrations across the digital stack with the IT/Architecture teams: LMS platforms; Drupal (web/content management); Medusa (headless / composable commerce); and Pimcore (PIM / MDM / DAM / DXP) and any other platforms within our PMO portfolio.
  • Have basic understanding of systems integration and data-migration initiatives — connecting platforms through REST / GraphQL APIs, SSO, SCORM/AICC and other LMS standards, and iPaaS / middleware with rigorous planning for data quality, cutover, and rollback.
  • Translate between business stakeholders and engineering / architecture teams, ensuring requirements, sequencing, and technical trade-offs are clearly understood on both sides.
  • Maintain a program-level view of architecture dependencies, technical risk, and non-functional requirements (security, performance, scalability, regulatory compliance).
AI Enablement in Portfolio amp; Delivery
  • Apply AI across the portfolio lifecycle: use generative AI for status synthesis, document and plan drafting, and meeting summarization; predictive analytics for forecasting delays, resource constraints; and emerging agentic capabilities for proactive risk surfacing.
  • Strengthen the data foundation (data quality, governance, and structure) that makes AI-assisted portfolio decisioning reliable and trustworthy.
  • Evaluate and responsibly adopt AI features within the toolchain (e.g., Atlassian Intelligence, Power BI Copilot, platform-native AI such as Pimcore’s automation/Copilot capabilities), establishing sensible guardrails for governance and oversight.
  • Support AI-related delivery initiatives across the platforms (e.g., personalization, content/data enrichment, intelligent search), partnering with product and engineering on scope and value.
Tooling, Reporting amp; Insight
  • Run the portfolio in the Atlassian suite — Jira Cloud (intake, epics/initiatives, roadmaps, Advanced Roadmaps/Plans, Agile boards) and Confluence (governance documentation, decision logs, knowledge management).
  • Build executive-grade reporting and dashboards in Power BI, Jira or platforms such as Big Picture (and Excel), turning portfolio and delivery data into clear, actionable insight for leadership to visualize.
  • Define and track the metrics that matter — delivery predictability, flow/throughput, value realized, ROI, and risk exposure — and tell the story behind the numbers.
Stakeholder, Leadership amp; Cross-Functional Influence
  • Act as the bridge between executives, functional leaders, product, engineering, and delivery teams — translating strategy into execution and execution status back into strategic insight.
  • Accountable for ensuring that all discussions result in clear decisions, defined ownership, actionable next steps, agreed scope boundaries, documented trade-offs, and transparent follow-through.
  • Demonstrates the ability to communicate with clarity, professionalism, and appropriate candor; facilitate alignment across diverse stakeholders; and accurately represent differing viewpoints while maintaining objectivity and organizational priorities.
  • Facilitate difficult prioritization and trade-off conversations with executive presence, building alignment among stakeholders with competing interests by providing clear recommendations, impact assessments, trade-off analyses to maintain alignment with portfolio objectives, timelines, budgets, and organizational priorities.
  • Provide coaching and support to project managers and workstream leads, and drive a culture of accountability, transparency, and continuous improvement across the PMO.
  • Provide resource allocation recommendations on capacity amp; projects’ needs (PMs, BSAs, etc.) based on projects’ plans, delivery and forecasted timelines.
  • Lead portfolio-level decision and escalation management paths, ensuring strategic, operational, and delivery risks are identified early, routed through the appropriate governance channels, and resolved in a timely manner.
Qualifications
Education amp; Certifications
  • Bachelor’s degree in Business, Finance, IT, Computer Science, or a related field required; MBA preferred.
  • PMP, PgMP, or PfMP required.
  • Agile / scaling certifications strongly preferred (e.g., CSM/PSM, SAFe — SA / SPC / RTE, or Certified LeSS Practitioner).
  • Change-management certification (e.g., PROSCI) a plus.
  • AI / data-related credentials or demonstrable applied experience a plus.
Experience
  • 4-6+ years in program and portfolio management, including 2–3+ years leading enterprise transformation or technology-platform programs.
  • Demonstrated success standing up or operating PMOs and managing portfolios in dynamic, multi-project environments.
  • Hands-on delivery experience with web/content, commerce, PIM/DXP, or LMS platforms — such as Drupal, Medusa (or comparable headless/composable commerce), Pimcore (or comparable PIM/MDM/DXP), and learning management systems.
  • Proven experience in IT systems integrations and data migrations (APIs, SSO, ERP/CRM, content or catalog migrations); ERP / HR / Finance system consolidation experience a plus.
  • Strong background in cross-functional governance, executive reporting, and resource management, with exposure to corporate finance concepts (ROI, synergies, cost savings).
Technical Skills
  • Atlassian suite: advanced proficiency with Jira Cloud and Confluence (boards, roadmaps/Plans, automation, reporting).
  • Prioritization amp; metrics: fluency with RICE, weighted scoring, and value-vs-effort prioritization, plus Agile flow and delivery metrics.
  • Reporting amp; analytics: Power BI/Jira Dashboards/Big Picture and Excel skills for portfolio dashboards and executive reporting.
  • Architecture literacy: working understanding of APIs (REST/GraphQL), SSO, SCORM/AICC, headless/composable architecture, and integration/iPaaS patterns — enough to lead credibly, partner with engineering, and assess technical risk.
  • AI fluency: practical familiarity with generative, predictive, and agentic AI in a delivery/PMO context, and the judgment to apply it responsibly.
  • Methodologies: deep command of Agile, plus scaled frameworks (SAFe, LeSS) and Lean Portfolio Management; familiarity with MS Project / Visio / SharePoint useful.
Soft Skills
  • Executive presence and the ability to facilitate difficult prioritization and trade-off discussions.
  • Outstanding communicator, written and verbal, across technical and business audiences.
  • Ability to influence without direct authority and drive alignment across diverse stakeholders.
  • Strong facilitation, negotiation, and conflict-resolution skills.
  • High adaptability, resilience, and comfort operating in ambiguous, fast-changing environments.
  • Curiosity and a growth mindset — especially toward emerging tools and AI-enabled ways of working.
We Offer Great Benefits:
  • Dental Coverage
  • Competitive salary and annual bonus
  • Paid Time off and company recognized holidays
  • Health amp; Medical Supplemental coverage
  • Emergency Travel Coverage
  • Mental Health amp; Virtual Care
  • Life amp; Accidental Coverage
Why This Role Matters
This position sits at the intersection of strategy, technology, and execution. As 360training scales its platforms and integrates new acquisitions, the Portfolio / Strategic Projects Lead is the operational anchor who ensures the right initiatives are prioritized, delivered with discipline, and connected into a coherent digital ecosystem — supported increasingly by AI-enabled insight and governance