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Senior Software Engineering Manager · Spring Health · Frisco, Texas

Gurusewak
Kalra

Senior Software Engineering Manager building AI-native products, high-impact teams, and modern engineering organizations.

I lead product engineering at the intersection of AI, enterprise SaaS, customer value, and growth. I help teams decide where AI creates meaningful leverage, build production-ready experiences, modernize how software is delivered, and develop engineers into broader technical leaders.

Leadership Impact

Engineering connected to customer and business outcomes.

$1.8M

Qualified expansion opportunities generated

$1.2M converted into closed opportunities

32%

Reduction in customer-support emails

Through AI-powered support experiences

28%

Increase in new monthly active users

Driven by product-led growth initiatives

$5M+

Operational savings generated

Through digital customer-support and engagement

19+

Countries reached

Expanding enterprise experiences globally

$20M

Enterprise contract influenced

Contributed to a landmark enterprise deal

5.5 → 7.8

Customer NPS improvement

Measurable customer experience lift

85% → 93%

Digital engagement increase

Across the customer platform

AI-Native Engineering

Led engineering teams building AI-powered customer support, knowledge retrieval, classification, routing, and agentic workflows.

32% support deflection

Product Strategy

Evolved Spring Insights into a customer-value platform with ROI analytics, clinical outcomes, and executive reporting.

$1.8M expansion pipeline

People Leadership

Led up to 11 engineers across two teams. Built hiring pipelines, coached engineers toward ownership, and developed senior engineers into technical leaders.

11 engineers led

Organizational Transformation

Helped lead Spring Health toward AI-native engineering: career ladders, interview design, AI fluency standards, and SDLC integration.

Company-wide impact

AI-Native Engineering

Building AI capability across products, teams, and engineering systems.

Not experiments. Not features. A durable operating model where AI is embedded in how products are built, teams are evaluated, and engineering organizations grow.

Product Strategy

Evaluate whether AI creates meaningful leverage. Compare with deterministic software, workflow automation, and data pipelines before committing.

  • Problem-first decision framework
  • AI vs. deterministic trade-off analysis
  • Value, cost, latency, and security assessment
  • Long-term maintainability planning

AI Architecture

Build production-ready AI systems with proper retrieval, grounding, evaluation, and human oversight rather than prototype-grade integrations.

  • RAG with semantic and keyword retrieval
  • Agentic workflows with domain semantics
  • MCP and structured tool definitions
  • Observability and evaluation loops

Engineering Workflow

Integrate AI across the full SDLC, from discovery and design through implementation, testing, review, and measurement.

  • AI-assisted discovery and specification
  • Accelerated implementation and code review
  • AI-supported testing and quality gates
  • Measuring delivery and quality outcomes

Talent Systems

Update career ladders, establish AI fluency expectations, and redesign the interview process so AI capability becomes a hiring and growth criterion.

  • IC and manager career ladder updates
  • AI fluency expectations at every level
  • AI-native interview design
  • Connecting AI capability to career growth

Organizational Adoption

Help the organization move from isolated AI experiments to durable, measured AI capability embedded in product thinking and engineering execution.

  • Coordinating cross-team AI pilots
  • Representing product-engineering concerns
  • Influencing reusable AI architecture
  • Measuring adoption through outcomes

Organizational Transformation · Spring Health

Before

AI as an optional productivity tool

  • AI used ad-hoc by individual engineers
  • No standards for AI in interviews or hiring
  • Career ladders silent on AI expectations
  • Architecture and tooling fragmented
  • No measurement of AI adoption or impact
After

AI as an intentional capability embedded in product thinking and engineering execution

  • AI fluency expected at every engineering level
  • Interview process assesses AI judgment
  • Career ladders updated with AI expectations
  • Reusable AI architecture and shared tooling
  • Adoption tracked through delivery and quality outcomes

Helped lead Spring Health's transition toward AI-native engineering as one contributor among a broader organization.

People & Organizational Leadership

Technology scales through people.

Led up to 11 engineers across two product teams. Hiring, performance management, career planning, coaching, and developing engineers into technical leaders.

Engineer Development Model

Stage: Executor

The engineer delivers well-scoped tasks on time with good quality. They do what's asked and do it well.

Coaching approach

  • Give clear scope and explicit success criteria
  • Pair on ambiguous problems to build confidence
  • Provide direct feedback on quality and pace
  • Build trust through consistent follow-through

Leadership Philosophy

Give engineers clarity, context, ownership, and direct feedback.

Help strong executors become owners, owners become technical leaders, and technical leaders become organizational multipliers.

Protect team focus during ambiguity and staffing pressure.

Manage underperformance directly and fairly, for the team's benefit.

Build psychologically safe but accountable environments.

Lead through cross-functional influence rather than authority alone.

Selected Leadership Stories

Where leadership met product, AI, and people.

Making Engineering AI-Native

Helped lead Spring Health's transition from AI as an optional tool to AI as an intentional capability embedded across career ladders, hiring, product development, and the full SDLC.

Career LaddersAI FluencyInterview DesignSDLC IntegrationAdoption Measurement
Company-wide engineering transformation

Evolving Spring Insights into a Customer-Value Platform

Led the engineering team that transformed an analytics feature into a customer-value platform with ROI measurement, clinical outcome tracking, executive reporting, and AI-powered engagement.

ROI AnalyticsClinical OutcomesExecutive ReportingAI SupportCustomer Retention
$1.8M expansion pipeline generated

AI-Powered Customer Support

Built an AI-powered support experience with knowledge retrieval, intent classification, ticket routing, deterministic guardrails, and human escalation paths.

Knowledge RetrievalClassificationRoutingGuardrailsObservability
32% reduction in support emails

Global Knowledge and Support Automation

Led the architecture and delivery of a global knowledge and support platform across 70+ sites, 9 languages, and 17 products with automated publishing and AI-assisted personalization.

70+ Sites9 Languages17 ProductsAutomated PublishingPersonalization
$5M+ operational savings

Scaling Product Experiences Globally

Expanded enterprise product experiences to more than 19 countries, coordinating across engineering, localization, design, and legal teams to build scalable, accessible international architecture.

19+ CountriesAccessibilityArchitectureCross-Team Coordination
$20M enterprise contract influenced

Career Journey

From engineer to organizational leader.

CodeSystemsProductsTeamsLeadersOrganizations

2022 – Present

Teams → Organizations

Senior Software Engineering Manager

Spring Health

Lead up to two product engineering teams (11 engineers). Built AI-native customer support, analytics, and insights platforms. Helped lead organizational AI transformation: career ladders, interview design, and AI fluency standards.

AI EngineeringPeople LeadershipProduct StrategyOrg Transformation

2021 – 2022

Products → Teams

Software Engineering Manager

Spring Health

Managed engineering team delivering customer-facing product experiences. Established engineering practices, hiring processes, and product-engineering collaboration frameworks.

Engineering ManagementHiringProduct Engineering

2019 – 2021

Systems → Products

Staff Software Engineer

LogMeIn

Technical leadership across global customer support and knowledge platforms. Led architecture for 70+ sites, 9 languages, 17 products. Contributed to $20M enterprise contract and $5M+ in operational savings.

Technical LeadershipGlobal PlatformsArchitectureEnterprise

2016 – 2019

Code → Systems

Technical Lead / Senior Engineer

LogMeIn

Led technical direction for customer experience products. Expanded platforms to 19+ countries. Improved sales demo satisfaction from 2.6 to 4.6.

Technical LeadInternational ExpansionCustomer Experience

2014 – 2016

Components → Features

Senior Software Engineer

Citrix

Delivered complex product features across enterprise SaaS products. Deep technical execution in large-scale systems.

Enterprise SaaSFull-StackScale

2012 – 2014

Individual Contributor

Software Developer

Egen Solutions

Started career building customer-facing web applications. First engineering role establishing foundations in product thinking and technical craft.

Web DevelopmentProduct Engineering

Personal

The same curiosity that builds systems also explores the world.

Engineering leadership is not just a professional identity. The way I approach exploration, learning, and ambiguity outside work is the same way I approach it inside.

33 States and Counting

Goal: all 50

Exploring the United States one state at a time, with a goal to visit all 50. Every trip is an exercise in curiosity.

Flying Lessons

Systems thinking from 2,000 ft

Took flying lessons and seriously considered becoming a pilot. Understanding systems from the cockpit changed how I think about complex technical decisions.

Titanic's Final Dinner

April 14, 1912 menu

Recreated the Titanic's final first-class dinner menu for friends, a research project disguised as a dinner party.

International Cultures

9 languages shipped

Strong interest in international cultures, languages, and global experiences. Nine languages in the support platforms I've helped build.

Cooking and Cuisine

Always experimenting

Cooking new cuisines as a form of exploration. Trying restaurants nobody has heard of. Finding signal in unexpected places.

Continuous Learning

Never stop building

From hands-on developer to engineering manager, each stage required unlearning as much as learning. Curiosity is the constant.

“Moving from a hands-on developer into engineering leadership was not about giving up the craft. It was about finding a bigger way to build.”

Contact

Let's build what comes next.

I'm interested in opportunities where I can lead AI-native product engineering, develop strong technical leaders, and connect engineering strategy with meaningful customer and business outcomes.

Frisco, Texas · Open to remote
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