This document discusses engineering challenges for scaling startups. It identifies challenges in people, process, and technology that startups face as they grow. For people, challenges include adopting new roles, prioritizing goals, and managing attrition. Process challenges involve setting structure, focus, and communication. Technology challenges involve maintaining system stability, moving from generalists to specialists, and upgrading infrastructure as the team grows. The document provides recommendations for addressing these challenges through a service mindset, transparency, flexibility, and learning from experienced peers.

1. Managing Engineering Challenges
with Startup Scaling
Sept 2021
Rohini Pradeep
Head of Product Engineering, People Platform for
Big Desk Segment

2. Gusto - All-In-One People Platform
Grow your business with a platform that supports your team

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The Story
Meet Jessica : A successful first-time tech startup CEO with tremendous growth potential for her product
and company. This is her first start up gig after 8 years as an engineer
Her problem
“What’s needed
for my company
to scale and be
successful?”
“How do I set my
teams up for
success to have the
right Outcome and
Impact ”
2
1

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Focus on Engineering
Challenges for Scaling Startups
GOAL

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Challenges with engineering scaling
PEOPLE PROCESS
TECHNOLOGY
STACK
• Vision
• Passing the hat
• New roles
• Goals and focus
• Service Mindset
• Old habits die hard
• Priorities and context switching
• Transparency
• Attrition
• Prototype to scale
• Bottlenecks
• System stability with team
growth
• Productivity, developer
tools
• Generalists to specialists
• Right team size

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People
Holistic View of the Business
Service centric mindset with Outcome and Impact focus for teams.
Empowerment, Empathy and Accountability
Growth mindset, empathy for change management, reinforcing positive accountability
Values
Engineering values that focus on Quality, Trust, Humility and Service, Pragmatism, Giving back to the Community
Representation, Inclusion, Social Impact and Equity (RISE)
Continue to build a diverse team with a great culture for rich product perspectives
People first culture

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Technology
1. Footnote
People first culture
Developer
productivity
and scaling
1
2
KPIs and
Metrics for
Success
3
Build vs
Buy
4
Budget and
planning
5
Flexible to
pivot based
on business
strategy
6
Upgrade
path for
technology
stack
7
Generalists
to domain
specific
teams

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Process
1. Footnote
Let’s play chess and not Whack-A-Mole
Structure with process, team
and organization
Focus and Priorities
Communication with
Stakeholders,
Transparency
Right fit for team
and business
Success Metrics
and ROI

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Peers, Partners and Strategy
● Lean in on trusted people who have been there, done
that
● Evaluate your technology strategy approach with your
peers and leaders in the industry
● Work with vendors and trusted partners for burst
capacity
● Align technology growth strategy with business
1. Footnote
You are not alone

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Key Takeaways
● Technology Scaling is unique to each company’s
experience
● Systems and processes in place to make growing
seamless
● Not mandated to add extra resources, but using the
resources right
● No rules set in stone or one-size fits all model in place
● Set of guidelines and recommendations from people
who have gone through something similar
1. Footnote