Chicago Sun-Times growth playbook

Replace the redirect with a welcome page: confirm the newsletters chosen, suggest one more (Sports readers get Halas Intrigue, Morning Edition readers get News Alerts), offer to create a free account to save preferences, and end with a soft membership ask that explains why the site is free ("readers fund ours"), with a small monthly amount pre-selected. Follow with a five-email welcome series that makes the first gift ask in email three, and track subscriber-to-member conversion by newsletter.

People who just gave their email are the warmest audience a newsroom has; a welcome page and series typically convert far better than a sitewide banner, and they grow known users at the same time.

[ ] Redirect replaced by a welcome page
[ ] Chosen newsletters confirmed
[ ] One suggested newsletter by interest
[ ] Free account offer to save preferences
[ ] Soft membership ask with monthly default
[ ] Five-email welcome series, ask in email three
[ ] Promotions opt-in shown as a choice
[ ] Campaign code for the welcome path
[ ] Subscriber-to-member report by newsletter

• Asking too soon

  Keep the page ask soft and lead with the newsletter value.

• Promotions opt-in complaints

  Make the promotional opt-in a visible choice.

• Your websiteThe newsletter hub (newsletter-hub.suntimes.com) offers five newsletters: Morning Edition, Sports, Halas Intrigue Bears Report, News Alerts and High School Sports; none in Spanish, on food and culture, or on politics. The page is rendered by a script (its HTML has no newsletter text for search engines). Its code shows that after "Thanks for subscribing! Watch your inbox for our newsletters." the reader is sent to the homepage five seconds later, and hub sign-ups are also added to "Promotions".Source
• HiringDirector of Growth & Acquisition (posted September 25, 2026): "leads Chicago Public Media's audience growth and member acquisition engine across all brands"; owns "Audience Awareness", "Audience Engagement", "Registration & Identity Development" and the "First membership transaction"; will "lead conversion optimization across landing pages, donation flows, registration experiences, and onboarding pathways"; measured on "registration and known-user growth", "CPA and acquisition efficiency", "first-year retention performance" and "growth of high-potential audience segments"; leads acquisition for "new product launching in FY27".Source
• Your websitesuntimes.com redirects to chicago.suntimes.com. The site has no paywall ("This site is free thanks to our community of supporters"); a sitewide banner says "Chicago needs watchdogs, and readers fund ours. Join them." (tracked as "FY27-SitewideBanner-Onsite") and the header Donate buttons are tracked as "MainDonationButton". The membership page lists the reader's impact and "our 2026 calendars", and its "Donate Now" buttons jump to an on-page widget; the app page says the e-Paper is "included with your Sun-Times print subscription and membership"; the footer offers "Donate Your Car" and "Gift Matching". The Sun-Times has been a 501(c)(3) in the Chicago Public Media family since 2022 and has won eight Pulitzer Prizes.Source
• HiringFundraising hiring: a Philanthropy Officer managing "a portfolio of 125 – 150 major donors with the capacity to make $5,000+ gifts" and a Director of Institutional Giving managing "50-80 foundations and corporations". Every post describes Chicago Public Media (WBEZ, the Chicago Sun-Times and Vocalo) as reaching "more than 3.3 million people weekly", "100% community-funded" and "powered by nearly 97,000 members".Source

Translate the banner and donation explainer on /la-voz pages, publish a Spanish membership page (why the newsroom is free, what members fund, monthly options), and promote it on the WhatsApp channel. Track Spanish-page gifts separately.

Readers give when they feel the newsroom is theirs, and the language of the ask is the clearest signal.

• Payment form still in English

  Translate the form labels or add guidance.

• Your websiteLa Voz (/la-voz): Spanish-language pages marked "es-US", "El mejor lugar para cobertura de noticias y cultura latina en Chicago", a WhatsApp channel ("Encuentra más noticias en nuestro canal de WhatsApp") and a guide for recent immigrants. On the same pages the banner, the "Donate" buttons and "Why are we asking for donations?" are in English, and the membership page is English only.Source
• HiringDirector of Growth & Acquisition (posted September 25, 2026): "leads Chicago Public Media's audience growth and member acquisition engine across all brands"; owns "Audience Awareness", "Audience Engagement", "Registration & Identity Development" and the "First membership transaction"; will "lead conversion optimization across landing pages, donation flows, registration experiences, and onboarding pathways"; measured on "registration and known-user growth", "CPA and acquisition efficiency", "first-year retention performance" and "growth of high-potential audience segments"; leads acquisition for "new product launching in FY27".Source
• Your websitesuntimes.com redirects to chicago.suntimes.com. The site has no paywall ("This site is free thanks to our community of supporters"); a sitewide banner says "Chicago needs watchdogs, and readers fund ours. Join them." (tracked as "FY27-SitewideBanner-Onsite") and the header Donate buttons are tracked as "MainDonationButton". The membership page lists the reader's impact and "our 2026 calendars", and its "Donate Now" buttons jump to an on-page widget; the app page says the e-Paper is "included with your Sun-Times print subscription and membership"; the footer offers "Donate Your Car" and "Gift Matching". The Sun-Times has been a 501(c)(3) in the Chicago Public Media family since 2022 and has won eight Pulitzer Prizes.Source

Reserve fixed space for every ad slot, the sitewide banner and embeds; load the donation banner in reserved space; and set image dimensions. Track CLS by template (article, section, homepage) and confirm in the 28-day field data.

Stable pages keep readers on articles longer and make taps on Donate and newsletter buttons land where people meant.

• Ad revenue concerns

  Collapse empty slots only below the fold.

• Google PageSpeedChrome UX Report (real visitors, chicago.suntimes.com): loading passes (LCP 2.4s at the 75th percentile, but 10% slower than a year ago) and responsiveness passes (INP 161 ms), while layout shift fails at 0.23 (the limit is 0.1).Source
• Your websitesuntimes.com redirects to chicago.suntimes.com. The site has no paywall ("This site is free thanks to our community of supporters"); a sitewide banner says "Chicago needs watchdogs, and readers fund ours. Join them." (tracked as "FY27-SitewideBanner-Onsite") and the header Donate buttons are tracked as "MainDonationButton". The membership page lists the reader's impact and "our 2026 calendars", and its "Donate Now" buttons jump to an on-page widget; the app page says the e-Paper is "included with your Sun-Times print subscription and membership"; the footer offers "Donate Your Car" and "Gift Matching". The Sun-Times has been a 501(c)(3) in the Chicago Public Media family since 2022 and has won eight Pulitzer Prizes.Source

Render the newsletter list in the page HTML with a page for each newsletter, and add a one-click sign-up box for the matching newsletter to the Bears, Sports, High School Sports and news section pages.

Readers subscribe to what they are already reading; a Bears fan on a Bears page is the best Halas Intrigue prospect.

• Box fatigue

  One box per page.

• Your websiteThe newsletter hub (newsletter-hub.suntimes.com) offers five newsletters: Morning Edition, Sports, Halas Intrigue Bears Report, News Alerts and High School Sports; none in Spanish, on food and culture, or on politics. The page is rendered by a script (its HTML has no newsletter text for search engines). Its code shows that after "Thanks for subscribing! Watch your inbox for our newsletters." the reader is sent to the homepage five seconds later, and hub sign-ups are also added to "Promotions".Source
• Your websiteNavigation and channels: Games (Chicago Mini Crossword, Full Crossword, Sudoku, Word Flower, Word Search), the Halas Intrigue podcast, the Fran Spielman Show, "Who's My Alderperson?", a 2026 Illinois voter guide, Death Notices, the e-Paper, an app and a WBEZ live stream. The YouTube channel has about 129,000 subscribers, 8,431 videos and 71.6 million views; the site ranks around 6,000th worldwide on the Tranco list.Source
• HiringDirector of Growth & Acquisition (posted September 25, 2026): "leads Chicago Public Media's audience growth and member acquisition engine across all brands"; owns "Audience Awareness", "Audience Engagement", "Registration & Identity Development" and the "First membership transaction"; will "lead conversion optimization across landing pages, donation flows, registration experiences, and onboarding pathways"; measured on "registration and known-user growth", "CPA and acquisition efficiency", "first-year retention performance" and "growth of high-potential audience segments"; leads acquisition for "new product launching in FY27".Source

Set one pattern (brand, channel, placement, creative, fiscal year), apply it to every on-site placement and email, document it, and add a check before any campaign goes live.

Clean codes are what let the growth team compare CPA and first-gift rates across brands and channels.

• Breaking history

  Keep a mapping table.

• HiringRevenue Operations Lead (posted August 14, 2026): the coordination layer "across both the Growth & Acquisition and Lifecycle & Retention engines"; responsibilities include "standardizing campaign naming conventions, tracking structures", "business rules governing payment routing, retry logic, fraud prevention" and "overseeing donation platform governance to ensure alignment with audience experience, conversion performance".Source
• Your websitesuntimes.com redirects to chicago.suntimes.com. The site has no paywall ("This site is free thanks to our community of supporters"); a sitewide banner says "Chicago needs watchdogs, and readers fund ours. Join them." (tracked as "FY27-SitewideBanner-Onsite") and the header Donate buttons are tracked as "MainDonationButton". The membership page lists the reader's impact and "our 2026 calendars", and its "Donate Now" buttons jump to an on-page widget; the app page says the e-Paper is "included with your Sun-Times print subscription and membership"; the footer offers "Donate Your Car" and "Gift Matching". The Sun-Times has been a 501(c)(3) in the Chicago Public Media family since 2022 and has won eight Pulitzer Prizes.Source
• Your websiteThe newsletter hub (newsletter-hub.suntimes.com) offers five newsletters: Morning Edition, Sports, Halas Intrigue Bears Report, News Alerts and High School Sports; none in Spanish, on food and culture, or on politics. The page is rendered by a script (its HTML has no newsletter text for search engines). Its code shows that after "Thanks for subscribing! Watch your inbox for our newsletters." the reader is sent to the homepage five seconds later, and hub sign-ups are also added to "Promotions".Source
• HiringDirector of Growth & Acquisition (posted September 25, 2026): "leads Chicago Public Media's audience growth and member acquisition engine across all brands"; owns "Audience Awareness", "Audience Engagement", "Registration & Identity Development" and the "First membership transaction"; will "lead conversion optimization across landing pages, donation flows, registration experiences, and onboarding pathways"; measured on "registration and known-user growth", "CPA and acquisition efficiency", "first-year retention performance" and "growth of high-potential audience segments"; leads acquisition for "new product launching in FY27".Source

Add a short "Members get" block near the first Donate button: e-Paper access, the calendar at a stated level, member newsletters or events. Keep impact first and benefits second, and test the order.

A tangible thank-you raises conversion and lets the team use benefits in ads.

• Transactional feel

  Lead with mission.

• Your websitesuntimes.com redirects to chicago.suntimes.com. The site has no paywall ("This site is free thanks to our community of supporters"); a sitewide banner says "Chicago needs watchdogs, and readers fund ours. Join them." (tracked as "FY27-SitewideBanner-Onsite") and the header Donate buttons are tracked as "MainDonationButton". The membership page lists the reader's impact and "our 2026 calendars", and its "Donate Now" buttons jump to an on-page widget; the app page says the e-Paper is "included with your Sun-Times print subscription and membership"; the footer offers "Donate Your Car" and "Gift Matching". The Sun-Times has been a 501(c)(3) in the Chicago Public Media family since 2022 and has won eight Pulitzer Prizes.Source
• HiringDirector of Growth & Acquisition (posted September 25, 2026): "leads Chicago Public Media's audience growth and member acquisition engine across all brands"; owns "Audience Awareness", "Audience Engagement", "Registration & Identity Development" and the "First membership transaction"; will "lead conversion optimization across landing pages, donation flows, registration experiences, and onboarding pathways"; measured on "registration and known-user growth", "CPA and acquisition efficiency", "first-year retention performance" and "growth of high-potential audience segments"; leads acquisition for "new product launching in FY27".Source

Offer game-day extras that need a free account or email: live chat during games, a postgame newsletter within an hour, and picks contests. Link every vertical video to the Halas Intrigue newsletter.

Sports fans come back every week, so registration from them is durable and grows the pool of future members.

• Fans dislike sign-ups

  Keep core coverage free.

• HiringDeputy Sports Editor (posted October 16, 2026): will "drive social-first and video-forward storytelling, including vertical video, live coverage" on Instagram, TikTok and YouTube and find "stories, personalities and franchises with strong potential for recurring audience engagement". A Deputy Managing Editor, News Desk is also being hired.Source
• Your websiteThe newsletter hub (newsletter-hub.suntimes.com) offers five newsletters: Morning Edition, Sports, Halas Intrigue Bears Report, News Alerts and High School Sports; none in Spanish, on food and culture, or on politics. The page is rendered by a script (its HTML has no newsletter text for search engines). Its code shows that after "Thanks for subscribing! Watch your inbox for our newsletters." the reader is sent to the homepage five seconds later, and hub sign-ups are also added to "Promotions".Source
• Your websiteNavigation and channels: Games (Chicago Mini Crossword, Full Crossword, Sudoku, Word Flower, Word Search), the Halas Intrigue podcast, the Fran Spielman Show, "Who's My Alderperson?", a 2026 Illinois voter guide, Death Notices, the e-Paper, an app and a WBEZ live stream. The YouTube channel has about 129,000 subscribers, 8,431 videos and 71.6 million views; the site ranks around 6,000th worldwide on the Tranco list.Source
• HiringDirector of Growth & Acquisition (posted September 25, 2026): "leads Chicago Public Media's audience growth and member acquisition engine across all brands"; owns "Audience Awareness", "Audience Engagement", "Registration & Identity Development" and the "First membership transaction"; will "lead conversion optimization across landing pages, donation flows, registration experiences, and onboarding pathways"; measured on "registration and known-user growth", "CPA and acquisition efficiency", "first-year retention performance" and "growth of high-potential audience segments"; leads acquisition for "new product launching in FY27".Source

Let players save streaks, stats and unfinished puzzles with a free account, add a weekly games newsletter, and show a member thank-you on milestones (100-day streak).

Games are the most repeat-visit product a news site has; streaks give people a reason to register.

• Login friction

  Allow play without account.

• Your websiteNavigation and channels: Games (Chicago Mini Crossword, Full Crossword, Sudoku, Word Flower, Word Search), the Halas Intrigue podcast, the Fran Spielman Show, "Who's My Alderperson?", a 2026 Illinois voter guide, Death Notices, the e-Paper, an app and a WBEZ live stream. The YouTube channel has about 129,000 subscribers, 8,431 videos and 71.6 million views; the site ranks around 6,000th worldwide on the Tranco list.Source
• HiringDirector of Growth & Acquisition (posted September 25, 2026): "leads Chicago Public Media's audience growth and member acquisition engine across all brands"; owns "Audience Awareness", "Audience Engagement", "Registration & Identity Development" and the "First membership transaction"; will "lead conversion optimization across landing pages, donation flows, registration experiences, and onboarding pathways"; measured on "registration and known-user growth", "CPA and acquisition efficiency", "first-year retention performance" and "growth of high-potential audience segments"; leads acquisition for "new product launching in FY27".Source
• Your websiteThe newsletter hub (newsletter-hub.suntimes.com) offers five newsletters: Morning Edition, Sports, Halas Intrigue Bears Report, News Alerts and High School Sports; none in Spanish, on food and culture, or on politics. The page is rendered by a script (its HTML has no newsletter text for search engines). Its code shows that after "Thanks for subscribing! Watch your inbox for our newsletters." the reader is sent to the homepage five seconds later, and hub sign-ups are also added to "Promotions".Source

Launch a weekly La Voz email, promote it on WhatsApp and La Voz pages, and include the Spanish membership ask in the welcome series.

Email turns followers into known users the team can thank and ask.

• Small team

  Curate existing stories.

• Your websiteLa Voz (/la-voz): Spanish-language pages marked "es-US", "El mejor lugar para cobertura de noticias y cultura latina en Chicago", a WhatsApp channel ("Encuentra más noticias en nuestro canal de WhatsApp") and a guide for recent immigrants. On the same pages the banner, the "Donate" buttons and "Why are we asking for donations?" are in English, and the membership page is English only.Source
• Your websiteThe newsletter hub (newsletter-hub.suntimes.com) offers five newsletters: Morning Edition, Sports, Halas Intrigue Bears Report, News Alerts and High School Sports; none in Spanish, on food and culture, or on politics. The page is rendered by a script (its HTML has no newsletter text for search engines). Its code shows that after "Thanks for subscribing! Watch your inbox for our newsletters." the reader is sent to the homepage five seconds later, and hub sign-ups are also added to "Promotions".Source
• HiringDirector of Growth & Acquisition (posted September 25, 2026): "leads Chicago Public Media's audience growth and member acquisition engine across all brands"; owns "Audience Awareness", "Audience Engagement", "Registration & Identity Development" and the "First membership transaction"; will "lead conversion optimization across landing pages, donation flows, registration experiences, and onboarding pathways"; measured on "registration and known-user growth", "CPA and acquisition efficiency", "first-year retention performance" and "growth of high-potential audience segments"; leads acquisition for "new product launching in FY27".Source

Add a short note to both donation pages ("The Sun-Times and WBEZ are one nonprofit newsroom"), show cross-brand benefits, and share donor records so members are not asked twice.

Clarity avoids double asks and helps members feel part of a larger newsroom.

• Brand confusion

  Keep each brand's voice.

• Competitor researchBlock Club Chicago: "a nonprofit news organization dedicated to delivering reliable, nonpartisan and essential coverage of Chicago's diverse neighborhoods"; the Chicago Tribune: "Chicago News, Sports, Weather, Business & Things to Do". Sister brand WBEZ takes gifts on a separate site, donate.wbez.org ("Support WBEZ | WBEZ Membership").See the research Source
• HiringFundraising hiring: a Philanthropy Officer managing "a portfolio of 125 – 150 major donors with the capacity to make $5,000+ gifts" and a Director of Institutional Giving managing "50-80 foundations and corporations". Every post describes Chicago Public Media (WBEZ, the Chicago Sun-Times and Vocalo) as reaching "more than 3.3 million people weekly", "100% community-funded" and "powered by nearly 97,000 members".Source
• Your websitesuntimes.com redirects to chicago.suntimes.com. The site has no paywall ("This site is free thanks to our community of supporters"); a sitewide banner says "Chicago needs watchdogs, and readers fund ours. Join them." (tracked as "FY27-SitewideBanner-Onsite") and the header Donate buttons are tracked as "MainDonationButton". The membership page lists the reader's impact and "our 2026 calendars", and its "Donate Now" buttons jump to an on-page widget; the app page says the e-Paper is "included with your Sun-Times print subscription and membership"; the footer offers "Donate Your Car" and "Gift Matching". The Sun-Times has been a 501(c)(3) in the Chicago Public Media family since 2022 and has won eight Pulitzer Prizes.Source
• HiringRevenue Operations Lead (posted August 14, 2026): the coordination layer "across both the Growth & Acquisition and Lifecycle & Retention engines"; responsibilities include "standardizing campaign naming conventions, tracking structures", "business rules governing payment routing, retry logic, fraud prevention" and "overseeing donation platform governance to ensure alignment with audience experience, conversion performance".Source

Add a membership and newsletter call to action to descriptions, end screens and pinned comments, a short "who pays for this" clip, and a members-only live Q&A each month.

Video audiences are large and loyal but rarely asked; a clear path turns some into known users and members.

• Viewers outside Chicago

  Lead with newsletters.

• Your websiteNavigation and channels: Games (Chicago Mini Crossword, Full Crossword, Sudoku, Word Flower, Word Search), the Halas Intrigue podcast, the Fran Spielman Show, "Who's My Alderperson?", a 2026 Illinois voter guide, Death Notices, the e-Paper, an app and a WBEZ live stream. The YouTube channel has about 129,000 subscribers, 8,431 videos and 71.6 million views; the site ranks around 6,000th worldwide on the Tranco list.Source
• HiringDeputy Sports Editor (posted October 16, 2026): will "drive social-first and video-forward storytelling, including vertical video, live coverage" on Instagram, TikTok and YouTube and find "stories, personalities and franchises with strong potential for recurring audience engagement". A Deputy Managing Editor, News Desk is also being hired.Source
• HiringDirector of Growth & Acquisition (posted September 25, 2026): "leads Chicago Public Media's audience growth and member acquisition engine across all brands"; owns "Audience Awareness", "Audience Engagement", "Registration & Identity Development" and the "First membership transaction"; will "lead conversion optimization across landing pages, donation flows, registration experiences, and onboarding pathways"; measured on "registration and known-user growth", "CPA and acquisition efficiency", "first-year retention performance" and "growth of high-potential audience segments"; leads acquisition for "new product launching in FY27".Source

Give each steward a newsletter template, a sign-up page per neighborhood, Sun-Times and WBEZ story feeds, and a shared account system, and report sign-ups per neighborhood.

Hyperlocal email is what readers value most, and it builds known users before any ask.

• Overlap with Block Club

  Lead with community voice.

• HiringCommunity Stewards Lead (posted October 9, 2026): Chicago.com is "a new digital platform from Chicago Public Media" with online communities "serving five Chicago communities", each supported by a paid Community Steward; the lead tracks "growth, retention, and engagement" and will "help stewards develop newsletters", with possible expansion to more neighborhoods. Chicago.com describes itself as "Local guides, community conversation, and news from every Chicago newsroom, gathered in one place."Source
• HiringDirector of Growth & Acquisition (posted September 25, 2026): "leads Chicago Public Media's audience growth and member acquisition engine across all brands"; owns "Audience Awareness", "Audience Engagement", "Registration & Identity Development" and the "First membership transaction"; will "lead conversion optimization across landing pages, donation flows, registration experiences, and onboarding pathways"; measured on "registration and known-user growth", "CPA and acquisition efficiency", "first-year retention performance" and "growth of high-potential audience segments"; leads acquisition for "new product launching in FY27".Source
• Competitor researchBlock Club Chicago: "a nonprofit news organization dedicated to delivering reliable, nonpartisan and essential coverage of Chicago's diverse neighborhoods"; the Chicago Tribune: "Chicago News, Sports, Weather, Business & Things to Do". Sister brand WBEZ takes gifts on a separate site, donate.wbez.org ("Support WBEZ | WBEZ Membership").See the research Source

Send a welcome, an "your gift at work" story at day 30, an invitation to an event or e-Paper at day 60 and a survey at day 90, and switch one-time givers to monthly with a one-click offer.

Early engagement predicts renewal.

• Too many emails

  Merge with newsletters.

• HiringDirector of Growth & Acquisition (posted September 25, 2026): "leads Chicago Public Media's audience growth and member acquisition engine across all brands"; owns "Audience Awareness", "Audience Engagement", "Registration & Identity Development" and the "First membership transaction"; will "lead conversion optimization across landing pages, donation flows, registration experiences, and onboarding pathways"; measured on "registration and known-user growth", "CPA and acquisition efficiency", "first-year retention performance" and "growth of high-potential audience segments"; leads acquisition for "new product launching in FY27".Source
• Your websitesuntimes.com redirects to chicago.suntimes.com. The site has no paywall ("This site is free thanks to our community of supporters"); a sitewide banner says "Chicago needs watchdogs, and readers fund ours. Join them." (tracked as "FY27-SitewideBanner-Onsite") and the header Donate buttons are tracked as "MainDonationButton". The membership page lists the reader's impact and "our 2026 calendars", and its "Donate Now" buttons jump to an on-page widget; the app page says the e-Paper is "included with your Sun-Times print subscription and membership"; the footer offers "Donate Your Car" and "Gift Matching". The Sun-Times has been a 501(c)(3) in the Chicago Public Media family since 2022 and has won eight Pulitzer Prizes.Source
• HiringRevenue Operations Lead (posted August 14, 2026): the coordination layer "across both the Growth & Acquisition and Lifecycle & Retention engines"; responsibilities include "standardizing campaign naming conventions, tracking structures", "business rules governing payment routing, retry logic, fraud prevention" and "overseeing donation platform governance to ensure alignment with audience experience, conversion performance".Source

Turn on card updater services, smart retries, and a three-message recovery sequence (email, text, letter) with a one-click update link.

Recovering failed payments is the cheapest retention gain.

• Annoying members

  Stop after three messages.

• HiringRevenue Operations Lead (posted August 14, 2026): the coordination layer "across both the Growth & Acquisition and Lifecycle & Retention engines"; responsibilities include "standardizing campaign naming conventions, tracking structures", "business rules governing payment routing, retry logic, fraud prevention" and "overseeing donation platform governance to ensure alignment with audience experience, conversion performance".Source
• HiringDirector of Growth & Acquisition (posted September 25, 2026): "leads Chicago Public Media's audience growth and member acquisition engine across all brands"; owns "Audience Awareness", "Audience Engagement", "Registration & Identity Development" and the "First membership transaction"; will "lead conversion optimization across landing pages, donation flows, registration experiences, and onboarding pathways"; measured on "registration and known-user growth", "CPA and acquisition efficiency", "first-year retention performance" and "growth of high-potential audience segments"; leads acquisition for "new product launching in FY27".Source

Flag members whose giving rises or who give $500+, invite them to newsroom briefings, and pass the best prospects to the philanthropy team with notes.

Upgrades from loyal members are the most efficient major gift pipeline.

• Over-asking

  Coordinate asks across teams.

• HiringFundraising hiring: a Philanthropy Officer managing "a portfolio of 125 – 150 major donors with the capacity to make $5,000+ gifts" and a Director of Institutional Giving managing "50-80 foundations and corporations". Every post describes Chicago Public Media (WBEZ, the Chicago Sun-Times and Vocalo) as reaching "more than 3.3 million people weekly", "100% community-funded" and "powered by nearly 97,000 members".Source
• HiringDirector of Growth & Acquisition (posted September 25, 2026): "leads Chicago Public Media's audience growth and member acquisition engine across all brands"; owns "Audience Awareness", "Audience Engagement", "Registration & Identity Development" and the "First membership transaction"; will "lead conversion optimization across landing pages, donation flows, registration experiences, and onboarding pathways"; measured on "registration and known-user growth", "CPA and acquisition efficiency", "first-year retention performance" and "growth of high-potential audience segments"; leads acquisition for "new product launching in FY27".Source
• HiringRevenue Operations Lead (posted August 14, 2026): the coordination layer "across both the Growth & Acquisition and Lifecycle & Retention engines"; responsibilities include "standardizing campaign naming conventions, tracking structures", "business rules governing payment routing, retry logic, fraud prevention" and "overseeing donation platform governance to ensure alignment with audience experience, conversion performance".Source

Build one account used by newsletters, games, comments, Chicago.com and donations, with preferences and giving in one place, and personalize asks by what each reader uses.

A known reader is worth more across three brands than three partial ones.

• Large project

  Start with newsletters and games.

• HiringDirector of Growth & Acquisition (posted September 25, 2026): "leads Chicago Public Media's audience growth and member acquisition engine across all brands"; owns "Audience Awareness", "Audience Engagement", "Registration & Identity Development" and the "First membership transaction"; will "lead conversion optimization across landing pages, donation flows, registration experiences, and onboarding pathways"; measured on "registration and known-user growth", "CPA and acquisition efficiency", "first-year retention performance" and "growth of high-potential audience segments"; leads acquisition for "new product launching in FY27".Source
• HiringCommunity Stewards Lead (posted October 9, 2026): Chicago.com is "a new digital platform from Chicago Public Media" with online communities "serving five Chicago communities", each supported by a paid Community Steward; the lead tracks "growth, retention, and engagement" and will "help stewards develop newsletters", with possible expansion to more neighborhoods. Chicago.com describes itself as "Local guides, community conversation, and news from every Chicago newsroom, gathered in one place."Source
• Competitor researchBlock Club Chicago: "a nonprofit news organization dedicated to delivering reliable, nonpartisan and essential coverage of Chicago's diverse neighborhoods"; the Chicago Tribune: "Chicago News, Sports, Weather, Business & Things to Do". Sister brand WBEZ takes gifts on a separate site, donate.wbez.org ("Support WBEZ | WBEZ Membership").See the research Source
• HiringRevenue Operations Lead (posted August 14, 2026): the coordination layer "across both the Growth & Acquisition and Lifecycle & Retention engines"; responsibilities include "standardizing campaign naming conventions, tracking structures", "business rules governing payment routing, retry logic, fraud prevention" and "overseeing donation platform governance to ensure alignment with audience experience, conversion performance".Source

Package civic tools as funded programs: a year-round local government guide, ward pages and alerts, each underwritten by a foundation, with sign-ups for ward updates.

Funders support civic information, and the tools bring new readers into the registration funnel.

• Editorial independence

  Firewall and disclosure.

• Your websiteNavigation and channels: Games (Chicago Mini Crossword, Full Crossword, Sudoku, Word Flower, Word Search), the Halas Intrigue podcast, the Fran Spielman Show, "Who's My Alderperson?", a 2026 Illinois voter guide, Death Notices, the e-Paper, an app and a WBEZ live stream. The YouTube channel has about 129,000 subscribers, 8,431 videos and 71.6 million views; the site ranks around 6,000th worldwide on the Tranco list.Source
• HiringFundraising hiring: a Philanthropy Officer managing "a portfolio of 125 – 150 major donors with the capacity to make $5,000+ gifts" and a Director of Institutional Giving managing "50-80 foundations and corporations". Every post describes Chicago Public Media (WBEZ, the Chicago Sun-Times and Vocalo) as reaching "more than 3.3 million people weekly", "100% community-funded" and "powered by nearly 97,000 members".Source
• HiringDirector of Growth & Acquisition (posted September 25, 2026): "leads Chicago Public Media's audience growth and member acquisition engine across all brands"; owns "Audience Awareness", "Audience Engagement", "Registration & Identity Development" and the "First membership transaction"; will "lead conversion optimization across landing pages, donation flows, registration experiences, and onboarding pathways"; measured on "registration and known-user growth", "CPA and acquisition efficiency", "first-year retention performance" and "growth of high-potential audience segments"; leads acquisition for "new product launching in FY27".Source

Offer members a monthly live Halas Intrigue taping, early postgame analysis by email and an annual meet-the-writers night, promoted to sports newsletter readers.

Belonging-based perks convert fans without a paywall.

• Staff time

  Limit to monthly.

• Your websiteNavigation and channels: Games (Chicago Mini Crossword, Full Crossword, Sudoku, Word Flower, Word Search), the Halas Intrigue podcast, the Fran Spielman Show, "Who's My Alderperson?", a 2026 Illinois voter guide, Death Notices, the e-Paper, an app and a WBEZ live stream. The YouTube channel has about 129,000 subscribers, 8,431 videos and 71.6 million views; the site ranks around 6,000th worldwide on the Tranco list.Source
• HiringDeputy Sports Editor (posted October 16, 2026): will "drive social-first and video-forward storytelling, including vertical video, live coverage" on Instagram, TikTok and YouTube and find "stories, personalities and franchises with strong potential for recurring audience engagement". A Deputy Managing Editor, News Desk is also being hired.Source
• Your websitesuntimes.com redirects to chicago.suntimes.com. The site has no paywall ("This site is free thanks to our community of supporters"); a sitewide banner says "Chicago needs watchdogs, and readers fund ours. Join them." (tracked as "FY27-SitewideBanner-Onsite") and the header Donate buttons are tracked as "MainDonationButton". The membership page lists the reader's impact and "our 2026 calendars", and its "Donate Now" buttons jump to an on-page widget; the app page says the e-Paper is "included with your Sun-Times print subscription and membership"; the footer offers "Donate Your Car" and "Gift Matching". The Sun-Times has been a 501(c)(3) in the Chicago Public Media family since 2022 and has won eight Pulitzer Prizes.Source

Add a "Leave a legacy" page, mention it in member renewals and the e-Paper, and train the philanthropy team to follow up.

Older, loyal readers are most likely to consider planned gifts.

• Sensitive topic

  Gentle, opt-in wording.

• Your websiteNavigation and channels: Games (Chicago Mini Crossword, Full Crossword, Sudoku, Word Flower, Word Search), the Halas Intrigue podcast, the Fran Spielman Show, "Who's My Alderperson?", a 2026 Illinois voter guide, Death Notices, the e-Paper, an app and a WBEZ live stream. The YouTube channel has about 129,000 subscribers, 8,431 videos and 71.6 million views; the site ranks around 6,000th worldwide on the Tranco list.Source
• Your websitesuntimes.com redirects to chicago.suntimes.com. The site has no paywall ("This site is free thanks to our community of supporters"); a sitewide banner says "Chicago needs watchdogs, and readers fund ours. Join them." (tracked as "FY27-SitewideBanner-Onsite") and the header Donate buttons are tracked as "MainDonationButton". The membership page lists the reader's impact and "our 2026 calendars", and its "Donate Now" buttons jump to an on-page widget; the app page says the e-Paper is "included with your Sun-Times print subscription and membership"; the footer offers "Donate Your Car" and "Gift Matching". The Sun-Times has been a 501(c)(3) in the Chicago Public Media family since 2022 and has won eight Pulitzer Prizes.Source
• HiringFundraising hiring: a Philanthropy Officer managing "a portfolio of 125 – 150 major donors with the capacity to make $5,000+ gifts" and a Director of Institutional Giving managing "50-80 foundations and corporations". Every post describes Chicago Public Media (WBEZ, the Chicago Sun-Times and Vocalo) as reaching "more than 3.3 million people weekly", "100% community-funded" and "powered by nearly 97,000 members".Source

Add an "Ask the Sun-Times" box on section pages that needs an email, notify askers when their question is answered, and invite them to support the story.

Participation builds loyalty and known users at once.

• Too many questions

  Pick a few each week.

• Your websiteStories are shared with WBEZ (for example a Curious City explainer that ends with "More about our question-asker", a reader whose question started the story). The homepage has no H1 heading.Source
• HiringDirector of Growth & Acquisition (posted September 25, 2026): "leads Chicago Public Media's audience growth and member acquisition engine across all brands"; owns "Audience Awareness", "Audience Engagement", "Registration & Identity Development" and the "First membership transaction"; will "lead conversion optimization across landing pages, donation flows, registration experiences, and onboarding pathways"; measured on "registration and known-user growth", "CPA and acquisition efficiency", "first-year retention performance" and "growth of high-potential audience segments"; leads acquisition for "new product launching in FY27".Source

Add a visually hidden H1 ("Chicago Sun-Times: Chicago news, politics, sports and more") and check section pages for the same gap.

A basic fix that helps accessibility and search.

• Design change

  Use a hidden heading.

• Your websiteStories are shared with WBEZ (for example a Curious City explainer that ends with "More about our question-asker", a reader whose question started the story). The homepage has no H1 heading.Source