Full-Time

Director Software Engineering

Infrastructure

ClickUp

ClickUp

1,001-5,000 employees

SaaS platform for project management

Compensation Overview

$300k - $350k/yr

H1B Sponsorship Available

Remote in USA

Remote

Bachelor's, Master's

Category
Engineering Management (1)
Required Skills
Machine Learning
Computer Networking
SOC 2
AWS
Terraform
DevOps

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Requirements
  • Deep AWS infrastructure expertise, including EKS, VPC, transit gateway, DNS, and Terraform at scale, with strong architectural judgment and a track record of setting technical direction.
  • A track record of setting six- to twelve-month cloud roadmaps tied to enterprise, AI, and cost-related business outcomes.
  • Experience building partnerships across Product, Security, Site Reliability Engineering, and Database organizations and driving shared ownership across infrastructure and product boundaries.
  • Understanding of the product beyond its underlying infrastructure and willingness to extend ownership past traditional platform boundaries.
  • Proven experience growing and retaining senior-heavy, geographically distributed teams across full-time employee and contractor blends, including bench depth and succession planning.
  • Strong on-call instincts, incident ownership, and root-cause-analysis follow-through.
  • A security-first approach to authentication enforcement, network isolation, and shard boundaries.
  • Demonstrated interest in DevSecOps agents, AI-assisted infrastructure-as-code migrations, and skills-based automation.
  • A Bachelor of Science or Master of Science degree in Computer Science, Engineering, or equivalent experience.
  • At least 10 years of experience in infrastructure or platform engineering, including significant director-level experience managing distributed teams.
Responsibilities
  • Drive annual infrastructure savings by migrating data workloads to EKS and self-hosting key services such as OpenSearch.
  • Deprecate legacy frontend application load balancers and consolidate to one EKS-managed application load balancer per shard.
  • Eliminate single points of ownership across Networking, OpenSearch, and Terraform through cross-training and targeted hiring into coverage gaps.
  • Establish recurring alignment with Product, AI, Enterprise, and Security so infrastructure planning is driven by demand.
  • Deliver automated shard buildout through Backstage to remove manual work from enterprise scaling.
  • Reduce P0/P1 incidents attributed to Cloud Platform, including DNS and application load balancer misconfiguration, through hardened ingress patterns and Terraform policy guardrails that block unauthenticated public endpoints.
  • Own and deliver a roadmap covering agent enablement, centralized infrastructure as code, and deployment rollout acceleration tied to AI and Enterprise revenue goals.
  • Grow, develop, and retain a senior-heavy team distributed across the United States, Canada, and Europe, spanning full-time employees and contractors, with emphasis on succession planning and bench depth.
  • Own multi-million-dollar AWS spend accountability and contractor oversight with a savings-pipeline focus.
Desired Qualifications
  • AI/ML infrastructure experience, including scaling GPU orchestration, model-serving infrastructure, or cost-optimized inference compute.

ClickUp provides a SaaS platform for project management and productivity that helps teams plan, track, and collaborate in one place. It combines tasks, documents, time tracking, goal setting, and integrations with apps like Slack and Trello to centralize workflows. Revenue comes from subscription plans, including a free tier and paid tiers with more features and storage, billed monthly or annually. The platform competes by offering a wide set of features in a single platform for both small teams and large enterprises, aiming to reduce tool clutter and boost productivity.

Company Size

1,001-5,000

Company Stage

Series C

Total Funding

$537.2M

Headquarters

San Diego, California

Founded

2017

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Simplify Jobs

Simplify's Take

What believers are saying

  • February 4, 2026 disclosures showed $300 million ARR and an IPO-oriented executive hiring wave.
  • June 2026 Brain2 and Everything AI price packaging deepen monetization from existing customers.
  • ClickUp’s AI-agent narrative aligns with enterprise demand for context-rich automation across workflows.

What critics are saying

  • May 2026 layoffs cut 22% after 3,000 AI agents, signaling morale and execution strain.
  • Brain2’s 100% preference claims invite backlash if customer outcomes disappoint versus ChatGPT and Claude.
  • Asana, Monday.com, and Notion compress ClickUp’s AI differentiation; failed IPO readiness threatens survival.

What makes ClickUp unique

  • June 23, 2026 Brain2 unifies tasks, docs, decisions, conversations, and frontier models.
  • ClickUp’s June 2026 Brain MAX app extends company context beyond desktop workspaces.
  • The platform bundles project management, docs, chat, automations, and AI into one workspace.

Help us improve and share your feedback! Did you find this helpful?

Benefits

16" MacBook Pro

Moving Expenses

$200/mo commuter benefits

Team lunches every week

401(k) match up to 2%

Unlimited stacks, kombucha, and cold brew

Health & dental insurance

ClickUp swag

Team recognition rewards

Flexible PTO

Growth & Insights and Company News

Headcount

6 month growth

↑ 3%

1 year growth

↑ 4%

2 year growth

↑ 4%
Toggl
Jul 2nd, 2026
ClickUp and Toggl integration: track time without leaving ClickUp.

ClickUp and Toggl integration: track time without leaving ClickUp. If you use ClickUp to manage projects, integrating it with Toggl Track can make time tracking much more efficient. Instead of switching between multiple applications, you can track the time spent on tasks while staying focused on your work. In this guide, Toggl Widget'll explain how the ClickUp and Toggl integration works and why it's useful for teams and individuals alike. Why integrate Toggl with ClickUp? ClickUp helps you organize tasks, projects, and workflows, while Toggl Track records how much time each task takes. Using both together allows you to: * Track time on ClickUp tasks * Reduce manual time entry * Improve project reporting * Measure billable hours * Better estimate future projects The result is a smoother workflow with fewer interruptions. How the integration works. Depending on your setup, you can connect Toggl Track with ClickUp through integrations or automation tools. Once connected, you can associate your time entries with specific ClickUp tasks, making it easier to review both completed work and the time required to complete it. The available features may vary depending on your integration method. Who should use it? The ClickUp and Toggl integration is ideal for: * Project managers * Agencies * Developers * Marketing teams * Consultants * Small businesses If ClickUp is where your team plans its work, adding time tracking provides valuable insight into project effort. Benefits of using Toggl with ClickUp. Some of the biggest advantages include: * Better project estimates * More accurate timesheets * Reduced context switching * Improved reporting * Easier client billing Tracking time directly alongside your tasks helps ensure your records stay complete and accurate. Tips for better time tracking. To get the most from the integration: * Start your timer when you begin a task. * Stop it before moving to the next task. * Organize your entries using projects and tags. * Review reports regularly to identify productivity trends. Consistent tracking leads to better planning and more reliable project data. Keep tracking beyond your computer. The ClickUp integration keeps time tracking convenient while you're working at your desk. When you're away from your computer, Toggl Lockscreen Widget helps maintain that same convenience. Using Live Activities, your active Toggl timer appears directly on your iPhone Lock Screen, allowing you to check your elapsed time or stop your timer without opening the Toggl Track app. It's a simple way to keep your time tracking seamless wherever your work takes you.

Business Wire
Jun 23rd, 2026
ClickUp launches Brain², an AI platform with full company context that users preferred 100% of the time over ChatGPT

ClickUp has launched Brain², a reimagined AI platform that maintains full awareness of a company's knowledge, including tasks, documents, decisions and conversations. The system requires no setup or syncing and is designed to work across all teams. In blind evaluations, users preferred Brain² over standalone ChatGPT and Claude 100% of the time for real work tasks. The platform routes between Claude, GPT and Gemini based on requirements whilst injecting company context into every request. Brain² operates as a "multiplayer" AI, sharing memory across teams and continuing work after users log off. It creates production-quality slides, apps and dashboards, and integrates with Gmail, GitHub, Figma and Slack. The platform is SOC 2, ISO 42001, HIPAA and GDPR compliant, with no third-party AI provider storing or training on user data. Brain² is available across web, desktop, mobile and a new standalone app.

Financial Post
Jun 23rd, 2026
ClickUp launches brain2: your company's AI.

ClickUp launches brain2: your company's AI. Business Wire Published Jun 23, 2026 Article content Brain[2] knows your company, does the work, and gets smarter every day. Article content SAN DIEGO - ClickUp today announced the launch of Brain[2], a fundamental reimagining of its core AI platform. Brain[2] is the first AI with full awareness of all of your company's knowledge: every task, doc, decision, relationship, and conversation, structured and ready to work, powering every answer and execution across every team. No setup, no syncing, no starting cold. Article content Advertisement 1 Story continues below This advertisement has not loaded yet, but your article continues below. Article content "The model isn't the moat. What you can do with full context is. We've spent years building a layer of company intelligence that deeply understands how your team works. Brain[2] turns that into answers, decisions, and execution that are uniquely yours." Article content In blind head-to-head evaluations, users preferred Brain[2] 100% of the time over standalone ChatGPT and Claude when completing real tasks about their own work. The performance difference isn't model power; Brain[2] uses the cutting-edge frontier models. It outperforms these models because it injects the full context of a company's decisions, workflows, and history into every query, turning general-purpose intelligence into company-specific intelligence that informs action. Article content Top Stories Interested in more newsletters? Browse here. Article content "The model isn't the moat. What you can do with full context is. Article content We've spent years building a layer of company intelligence that deeply understands how your team works. Brain[2] turns that into answers, decisions, and execution that are uniquely yours." Article content - Zeb Evans, CEO and Founder, ClickUp Article content The Dawn of Multiplayer AI Article content Most AIs are built to work with one person at a time: no shared memory, no collaboration, no continued work after you log off. Brain[2] is multiplayer by default. Article content When a product manager builds a launch plan, Brain[2] already knows marketing's campaign timeline, engineering's sprint commitments, and sales' pipeline targets, so the plan accounts for all of it without a single sync meeting. When ops creates a dashboard, it pulls the right KPIs because Brain[2] has learned every team's definitions. When a new hire asks a question on day one, the answer is informed by every decision the company has already made. And Brain[2] can spin up AI agents that keep the work moving across the org, even when you log off. Article content It's a flywheel: every interaction makes Brain[2] smarter for the next person, the next team, the next workflow. The more your company uses it, the more valuable it becomes for everyone. Article content "Single-player AI hits a ceiling. Brain[2] is multiplayer by default: it knows every team, every workflow, every decision. So when anyone builds something, it works for the whole company, not just the person who prompted it." Article content - Jay Hack, Head of AI, ClickUp Article content What Makes Brain[2] Different Article content Brain[2] understands the full picture, and it shows in every response. Article content * Optimized Frontier Models with Full Company Context: Brain[2] routes between Claude, GPT, and Gemini based on what the work demands, or lets users choose the model they prefer, injecting your company's full context into every request. It flags overloaded sprints, surfaces conflicting priorities, and calls out timelines based on dependencies three teams deep. * Production-Quality Slides, Apps, Dashboards, and more: It creates truly polished artifacts such as slide decks, interactive dashboards, working websites, live data analysis, and more with a single prompt. Work that took hours now takes seconds. * Memory That Compounds: Brain[2] remembers your role, your preferences, your team's standards, and it carries that knowledge across the org. Every interaction makes it dramatically smarter. Every exchange sharpens the next one. * Every AI Tool in One: Brain[2] replaces standalone AI subscriptions across writing, research, coding, design, and analysis, all while connecting to Gmail, GitHub, Figma, Slack, and more. One tool, full context, up to 88% less AI spend. * Enterprise-Grade Security by Default: No third-party AI provider ever stores or trains on your data. SOC 2, ISO 42001, HIPAA, and GDPR compliant out of the box. Article content Advertisement 2 Story continues below This advertisement has not loaded yet, but your article continues below. Article content Availability Article content Brain[2] is live today for every ClickUp customer, everywhere: web, desktop, mobile, and the all-new Brain MAX standalone app, a dedicated mobile experience for talking, thinking, and building with Brain[2] wherever you are. Article content About ClickUp Article content ClickUp is the world's first Converged AI Workspace, a single place for humans and agents to work together with 100% context across all apps, data, and workflows. Trusted by more than 20 million users, ClickUp is on a mission to maximize human productivity. Article content View source version on businesswire.com: Article content Press Contact: Article content Advertisement 1

MultiSync Made Easy
Jun 9th, 2026
How to integrate ClickUp with Salesforce: step-by-step guide.

How to integrate ClickUp with Salesforce: step-by-step guide. By Team MultiSync Made Easy Published on June 9, 2026 | 3 Mins Read Connecting ClickUp with Salesforce is a crucial step for businesses that want to keep project management and customer data synchronized across both platforms. Without an integration, teams often spend time manually updating records, managing duplicate information, and switching between systems to access the latest data. To establish a secure ClickUp Salesforce integration, you first need ClickUp API credentials, which enable communication between ClickUp and Salesforce. In this step-by-step guide, Multisyncmadeasy'll show you how to generate a ClickUp API key and connect both platforms using MultiSync Made Easy for seamless data synchronization and data migration in Salesforce. A simple guide to integrating ClickUp with Salesforce. Step 1: First, sign in to your ClickUp account. If you do not have an account, create a new one and fill in all the required details. After signing up, verify your email address. Step 2: Complete the ClickUp setup by following the on-screen instructions and click Next to continue. Once the setup is complete, your ClickUp workspace will open. Step 3: click on the profile icon and then select settings. Step 4: In Settings, click ClickUp API, then select ClickUp API Settings. Next, click Create App, fill in all the required details, and click Create App. Step 5: Once the app is created, copy the Client ID and Client Secret. You'll need these details later while connecting ClickUp with Salesforce. Step 6: Now, log in to Salesforce, open the MultiSync Made Easy app, click All, and search for ClickUp. Step 7: select ClickUp, enter the client ID and client secret, then click save & authenticate. The Connect ClickUp page will appear. Click Connect Workspace, then click Complete Authentication, and finally click Refresh. Step 8: After completing authentication, you will see the dashboard. Click Import. Step 9: after clicking import, the import dashboard will appear. Click proceed. Step 10: click preview mapped data, then click validate field mapping, and finally click save field mapping. Step 11: Click Sync Data to start syncing data between ClickUp and Salesforce. Step 12: Once the sync is complete, your ClickUp and Salesforce records will be connected successfully through MultiSync Made Easy. Conclusion. So, that's it! By generating your ClickUp API credentials and completing the setup process, you can establish a seamless ClickUp Salesforce integration that keeps information connected across both platforms. This helps teams avoid repetitive data entry, reduce errors, and ensure everyone is working with the latest information. Managing data across multiple platforms can quickly become challenging, which is why Salesforce integration tools help businesses keep information connected and up to date. Whether you're looking to automate workflows or simplify data migration in Salesforce, connecting ClickUp and Salesforce can help create a more streamlined and productive way of working. The all-in-one Salesforce connector for future businesses. Step ahead with its robust and intelligent app that instantly integrates multiple platforms - even the unknown ones!

UC Today
May 29th, 2026
ClickUp cuts 22% of its workforce and dangles $1 million salaries for top AI performers.

ClickUp cuts 22% of its workforce and dangles $1 million salaries for top AI performers. The $4 billion productivity startup is deploying thousands of AI agents and rewarding those who can wield them Published: May 29, 2026 ClickUp has laid off roughly 286 employees - 22 percent of its 1,300-person workforce - and CEO Zeb Evans isn't framing it as bad news, but rather as a deliberate and strategic blueprint for what he believes the modern technology company should look like. "This wasn't about cutting costs," Evans wrote on X. "Most savings from this change will flow directly back into the people who stay." The carrot attached to that claim is striking: remaining employees who deliver "outsized impact using AI" could earn up to $1 million in base salary. It is a bold reimagining of how tech companies structure compensation, tying pay directly to the ability to extract value from AI rather than to tenure, title, or traditional output metrics. Agents in, headcount out. The restructuring follows an internal AI rollout in which ClickUp has deployed around 3,000 AI agents to handle complex operational tasks across the business, fundamentally changing what it expects from its employees. Staff are no longer expected to do the work themselves - they're expected to direct, manage, and quality-check the systems that do it for them. Evans' stated goal is to build a "100x org" - a company that punches far above its weight in output relative to headcount. Rather than measuring AI adoption by token consumption - a controversial practice critics have dubbed "tokenmaxxing" - ClickUp says it focuses on value created and time saved, a distinction Evans is apparently preparing to package into a customer-facing product. A vision already being lived? The broader AI-native model is already drawing significant investor confidence. Polsia - a one-year-old startup that handles software operations for solopreneurs - is run entirely by its founder and CEO, Ben Cera, with zero additional staff. The company just raised $30 million at a $250 million valuation, suggesting that the market is increasingly willing to back businesses built around AI from the ground up rather than retrofitted around it. Industry-Wide, but the returns aren't guaranteed. ClickUp is far from alone in making the pivot towards AI-first, with the broader tech industry undergoing a dramatic reorientation around AI talent and automation that is simultaneously eliminating roles and creating a new class of extraordinarily well-compensated specialists. But a recent Gartner survey complicates the narrative considerably. Around 80 percent of companies deploying autonomous AI have reduced headcount - yet meaningful financial returns remain elusive, raising serious questions about whether the productivity gains being promised are materialising in practice. Critics suggest some organisations are using unproven AI as a socially palatable reason to downsize, cutting costs under the cover of transformation while the technology quietly fails to deliver. The uncomfortable logic. Even on its own terms, Evans' vision carries an inherent tension that becomes harder to ignore the further the model is taken. "The people that automate their jobs with AI will always have a job," he wrote - but as AI agents absorb more functions and grow more capable, the ceiling for how many people any company actually needs keeps dropping, and today's AI orchestrator risks becoming tomorrow's redundancy. The honest read of Evans' model is that it creates a perpetual performance race - one where the goalposts move as AI capabilities improve, and employees must not just adopt AI, but continuously prove they are extracting more value from it than the technology could plausibly deliver on its own. For the 78 percent who kept their jobs, there's now a million-dollar incentive to prove the model right.