Gregory Swan

Co-Founder

San Diego, California, United States15 yrs 2 mos experience
AI Enabled

Key Highlights

  • Led ClickUp's content strategy from $30M to $300M ARR.
  • Scaled organic traffic from 37K to 2M+ monthly visitors.
  • Pioneered AI workflows for editorial processes.
Stackforce AI infers this person is a SaaS content strategist with expertise in narrative design and marketing.

Contact

Skills

Core Skills

Content StrategyContent MarketingContent Management

Other Skills

Narrative DesignNarrative JournalismMarket ResearchSEOAI WorkflowsProject ManagementCopywritingArtificial Intelligence (AI)Digital MarketingCustomer ServiceMicrosoft WordPowerPointMicrosoft OfficeMicrosoft ExcelResearch

About

I turn messy content operations into systems and narratives that actually scale. At ClickUp, I lead content strategy for a platform used by millions. On the side, I help early-stage SaaS teams stop winging it and start building content that compounds. What that looks like: positioning and messaging that sticks, website copy that converts, thought leadership that doesn't put people to sleep. 8+ years doing this. Still genuinely obsessed with the craft. → Need content strategy help? You can talk to me at copycafe.co ✏️ → Want weird takes on humanity? See my unhinged alien newsletter at weeklyprobe.com 👽

Experience

15 yrs 2 mos
Total Experience
2 yrs 2 mos
Average Tenure
3 mos
Current Experience

Clickup

Content and Narrative Design Lead

Feb 2026Present · 3 mos

Narrative DesignNarrative JournalismContent StrategyContent MarketingMarket Research

Pawcards.ai

Founder

Feb 2026Present · 3 mos

  • PawCards.AI is a free AI pet card generator that turns your dog or cat photo into beautiful custom greeting cards in 60 seconds. Choose from 12 art styles including watercolor, cartoon, and oil painting for 14 occasions like birthdays, holidays, and thank you cards.
  • Upload any pet photo. PawCards.AI transforms it into a stunning, printable card — perfect for birthdays, holidays, or just because.

The weekly probe

Founder 👽

May 2025Present · 1 yr · Milky Why❓ · Remote

  • The least classified classified brief in the galaxy. Transmitted by confused analysts studying Planet Dumb.
  • Read at your own risk: weeklyprobe.com/subscribe

Clickup

3 roles

Senior Content Marketing Manager

Promoted

Jun 2023Present · 2 yrs 11 mos

  • Owned ClickUp's global content strategy from $30M to $300M ARR and $4B valuation, spearheading content programs across web, campaigns, and acquisition during ClickUp's growth from 1M to 30M+ users.
  • Designed and evangelized ClickUp’s GTM narrative (Work Sprawl → Convergence), launched sprawl.work, flagship research reports, and an executive thought leadership engine via AI workflows and LinkedIn amplification.
  • Generated over $2M+ ARR in pipeline via B2B acquisition campaigns web, email, events, paid, and organic social.
  • Activated 300K+ free user Workspaces from B2C content programs via distribution of ClickUp guides surveys, and research on owned/paid channels.
  • Helped scale organic traffic from 37K to 2M+ visitors monthly by partnering with SEO to implement content optimization, localization, and automation strategies.
  • Cut acquisition costs on social by 66% through strategic creation + distribution of employee content programs, driving 5M impressions and 100K clicks to website.
  • Pioneered AI + agent workflows used company-wide for editorial reviews, product release notes, emails, webpages, and social with 2-4X increase in publishing speed.
Content StrategyContent MarketingMarket ResearchSEOAI Workflows

Content Manager

Promoted

Apr 2021Jun 2023 · 2 yrs 2 mos

  • Manage web content creation and editorial processes
  • Drive content campaigns with creative, product marketing, SEO, and paid media teams
  • Test, learn, and optimize copy and design across web content
  • Create the best user experience for ClickUp customers & visitors
Content ManagementSEOProject Management

Copywriter & Content Strategist

Sep 2020Apr 2021 · 7 mos

  • I was one of the first external marketing hires for ClickUp where I pioneered ClickUp's editorial systems to scale content quality and production across all marketing formats, including: landing pages, blogs, customer stories, direct response ads, video scripts, and more.
Content StrategyCopywriting

Copycafe.co

Founder ☕

Jan 2022Present · 4 yrs 4 mos

  • Skip the agency runaround. Get senior-level content strategy and execution from someone who helped build ClickUp's content operation from zero.
  • Trusted by teams backed by $1B+ in funding

Tinuiti

2 roles

Copywriter & Content Strategist

Oct 2019Aug 2020 · 10 mos

  • Grew organic traffic to Tinuiti.com by implementing strategic blog processes; keyword research, SEO best practices, and project management with product teams
  • Managed and grew a small team of freelance writers to scale content production
  • Implemented new coordination with product teams to source subject matter experts and topic opportunities to align with Tinuiti's newly acquired properties
  • Conducted regular keyword and competitor research to win and maintain rankings for competitive keywords
  • Develop customer-focused content strategies to support new product launches and agency initiatives

Content Specialist

Mar 2018Oct 2019 · 1 yr 7 mos

  • Expanded content strategy from an Amazon-focus to include B2B Facebook and Google ads content
  • Maintained ownership of Facebook and Google channel content with weekly reporting, topic
  • research, competitor analyses, and more
  • Regularly met with Google and Facebook representatives to keep ahead of important product launches
  • Took ownership of CPC Strategy's consumer studies program to expand topics and drive content lead generation
  • Created case studies, brand success stories, and brand interview features for CPC Strategy's blog
SEOContent StrategyProject Management

Capitol compliance management

Content Writer

Nov 2017Feb 2018 · 3 mos · Sacramento, California Area

  • Engage target community through blogs and other public-facing content.
  • Research, source, and write consistent and original content and edit all contributions of other departments.
  • Seek out opportunities for content syndication through external venues such as partner blogs and publishing platforms.
  • Identify, follow and participate in all relevant social media platforms.
  • Track and report on measurement criteria that demonstrates the relative success of blog content and other inbound marketing and communications programs.

Istanbul technical university

Native English Teacher

Feb 2015Jun 2017 · 2 yrs 4 mos · Istanbul, Turkey

  • Organized daily classes to improve speaking and reading comprehension, which raised year-end •Cambridge exam scores for junior-high students.
  • Researched and implemented newer publisher materials and learning strategies to increase student engagement and interest.
  • Analyzed and revised written examinations to improve student performance.
  • Held quarterly meetings and after-school tutoring to build rapport with parents and students.
  • Represented the department by writing and delivering ceremonial Republic Day speech to faculty and parents.

Doğa koleji

Native English Instructor

Aug 2013Jul 2014 · 11 mos · Istanbul, Turkey

  • Designed an after-school conversation club and early-morning exercises to provide extra-curricular opportunities for English learners.
  • Transcribed weekly newsletters from Turkish to English to engage English speaking parents.
  • Adapted new Pearson ESL materials to improve academic standards.
  • Delivered quarterly presentations to parents and faculty to build awareness and support for department programs.

Koç university

English Mentor & Group Leader

Jun 2013Aug 2013 · 2 mos · Istanbul, Turkey

  • Taught groups of children aged 4-12 conversational English during an English language summer camp program
  • Engaged children in daily English practice through a variety of summer camp activities: cooking, golf, parkour free running, poi, rhythm, photography and yoga
  • Provided hour-long classroom conversational lessons to help develop pronunciation, vocabulary, and speaking fluency
  • Served in a leadership role managing 4 other mentors and 15 students
  • Helped create group performance for parents

Apple

At-Home Advisor

May 2011Oct 2011 · 5 mos

  • Worked independently providing customer service for Apple computer products
  • Provided professional technical service for users of the Mac Operating System and related programs
  • Integrated phone communication and software skills to deliver timely and effective resolutions to customers

Kevin mccarty for state assembly

Political Intern

May 2010Jul 2010 · 2 mos

  • Building grassroots support by establishing face-to-face rapport with potential voters in downtown
  • Sacramento (District 9)
  • Campaigning door-to-door and via telephone by cold-calling potential voters
  • Planning neighbourhood coverage for campaign outreach in downtown Sacramento
  • Recruiting additional volunteers to expand ground campaign effort

Folsom cordova unified school district

Instructional Aid - Special Education

Oct 2009May 2013 · 3 yrs 7 mos

  • Provided one-on-one classroom support for mentally and physically handicapped students
  • Helped develop cognitive reading, writing, and mathematical skills for students with autism
  • Increased motor-skill development in low-functioning students through assisted exercise and physical activity
  • Assisted with toileting caregiving of medically fragile students
  • Assisted with teacher instruction of special needs students at various district sites (Folsom Middle School, Mitchell Middle School, Cordova High School, Vista del Lago High School)

Education

California State University-Sacramento

Bachelor of Arts (B.A.) — Political Science - International Relations

Jan 2008Jan 2013

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