Hire the Best Digital Strategists in Chicago, IL

More than 3,000 reviews on G2
Rating is 4.5 out of 5.
4.5/5
of Upwork by G2 peer reviewers
Lauren M.

Chicago, Illinois

$50/hr
5.0
8 jobs

Hi, I’m Lauren, a strategic digital marketing consultant and founder of Prize Digital with 10+ years of experience in sales and marketing and 5+ years of experience helping professional service firms and consultants turn authentic content into consistent leads and revenue. I specialize in building social-first marketing systems, short-form video strategies, and scalable content engines that help you grow without burning out. I’ve helped financial advising firms, accountants, lawyers, consultants, wellness brands, and small business owners build visibility, authority, and predictable growth, without wasting money on random posting. I also work closely with you through live coaching calls and record-with-you sessions, so you’re never stuck trying to figure out content alone. We plan it together, create it together, and turn it into high-performing assets you can reuse everywhere. About Me I run Prize Digital, a Chicago-based digital marketing agency focused on creating high-performing content ecosystems, not just “posting for the sake of posting.” Because I come from both sales and marketing, I understand how content connects directly to conversions, not just likes and views. My approach is honest, strategic, and no-fluff. I don’t believe in trendy tactics that don’t convert. I believe in building systems that: ✔ Attract the right clients ✔ Build trust fast ✔ Turn content into revenue ✔ Save you time ✔ Give you confidence on camera Whether you’re just starting out or ready to scale, my goal is to make sure your marketing actually supports your business. Services Offered 📱 Social Media Management (Done-For-You) 🎥 Short-Form Video Editing & Strategy (Reels, TikTok, Shorts) 📊 Digital Growth & Content Strategy 🎤 Live Content Coaching & Recording Sessions 🌐 Website & Funnel Strategy 📩 Email Marketing & Lead Magnets 🎙 Podcast & Long-Form Content Repurposing 📈 Paid Ads & Conversion Optimization Are you ready to: 🚫 STOP struggling with inconsistent content. 🚫 STOP guessing what to post. 🚫 STOP wasting time on marketing that doesn’t convert. 🚫 STOP feeling awkward or unsure on camera. You should be focused on running your business, not stressing over algorithms, captions, and content ideas. I’ll help you feel confident, prepared, and supported, so creating content stops feeling overwhelming and starts feeling doable. Key Achievements ✔ 10+ Years in Sales & Marketing ✔ 5+ Years Specializing in Service-Based Businesses ✔ Experience with founders, executives, accountants, lawyers, financial advisors, co-working spaces, consultants, professional firms, historians, salons, and wellness professionals. ✔ Built multi-channel content systems for clients nationwide ✔ Helped businesses increase leads, engagement, and authority ✔ Founder of a growing digital agency ✔ Video-first growth specialist Fun Fact When I’m not building content systems for my clients, you’ll usually find me learning the ropes of motherhood with my 9-month-old, testing new content formats, or nerding out over marketing trends, always looking for better ways to help you win. Let’s Chat Think we’d be a good fit? 👉 Click the green “Invite to Job” button 👉 Send me a message 👉 Let’s schedule a call If you’re ready to turn your content into a real growth engine, with support every step of the way, let’s make it happen.

  • Digital Marketing
  • Digital Marketing Strategy
  • Content Marketing
  • Social Media Strategy
  • Sales Funnel Implementation
  • Content Creation
  • LinkedIn Marketing
  • Instagram Marketing
  • YouTube Marketing
  • Personal Branding
  • Video Editing
  • Email Marketing
  • Marketing Automation
  • Squarespace
  • Advertising
Caroline H.

Chicago, Illinois

$50/hr
4.1
26 jobs

I’m a Marketing Strategist with over 8 years of experience as a former agency COO and a current agency owner. I work with founders and small teams to turn scattered marketing into a conversion-focused strategy with a clear content funnel, actionable checklists, and a system your team can actually follow. There's no such thing as "one-size fits all" when it comes to marketing your business. Trust an expert who will care about the success of your brand and create a personalized strategy fit for your goals. If you’re tired of posting without a plan (or relying on random bursts of inspiration), I’ll help you find clarity and consistency, so your marketing becomes easier to execute and more effective. CORE OFFERS: 🖥️ Marketing strategy + content funnel design (what to say, who it’s for, and how it moves people toward conversion) 📱Instagram strategy (positioning, content direction, funnel-based content planning, engagement approach) ✉️ Email marketing strategy (automated flow planning, funnel alignment, launch/support sequences, audience segmentation) 📋 Systems + SOPs (templates, checklists, dashboards, streamlined workflows built around your current tools & systems) I’m especially strong at taking big-picture goals and translating them into actionable, organized steps without bloated docs or vague direction. If you need a strategist to guide you towards effective marketing that is built for your team with the help of sustainable systems, let's talk. ⭐️ WHAT MY CLIENTS SAY ⭐️ "Caroline has been an invaluable asset to my business. Her intuitive nature has made her a key player on my team as she helps me hone my brand and have my personal voice heard. She is truly a joy to collaborate with on ideas, concepts, and next steps. She is not afraid to give you tips and advice which has really opened my eyes to how I can expand my business. If you need a loyal marketing team, I can't recommend Caroline enough!" -Colby Rebel "Caroline is one of the best people that I love working with when it comes to digital marketing. Because of her vast knowledge and constant need to improve, I always trust her to go above and beyond what is expected. It's a team effort when working with her — you don't just TELL her what to do. She'll let you know what works best, how to improve, and how we can collaborate to implement the changes." -Mae Tandoc "Far and above, I would recommend Caroline and her team as the team you need to pull it all together, understand your vision, and initiate concepts and ideas that help build your brand. A true find and a very happy client! From a concept to a website, fully managed social media presence, landing pages, email campaigns, and more... they truly know how to pull it together and alleviate your workload, not add to it. Highly recommend!" -Serena Kim "Caroline and her team went above and beyond in their services to us. Caroline is an incredibly talented designer with a very strong understanding of marketing. Would recommend her to any small business in the tech or e-commerce field! Her designs put our branding on the next level." -Will K. I live by the motto, "quality over quantity". In order to guarantee quality services to all my clients, I only work with clients I believe to be a good fit.

  • Digital Strategy
  • Social Media Management
  • Social Media Advertising
  • Instagram Story
  • Google Ads
  • Instagram
  • Social Media Marketing Strategy
  • Social Media Content Creation
  • TikTok Marketing
  • Instagram Marketing
  • Brand Identity & Guidelines
  • Shopify
  • Website
  • Social Media Content
Erica L.

Chicago, Illinois

$105/hr
5.0
5 jobs

ericalatack.com Erica is a Creative Director and Marketing Expert with 10+ years of experience driving growth for e-commerce brands across freelance, in-house, and agency roles. Specializing in creative direction, paid and organic social media, and brand marketing, Erica has a proven track record of developing high-performing campaigns, crafting compelling brand narratives, and driving growth across marketing channels. With a background in both creative and marketing, Erica has led initiatives for brands across industries including fashion, home goods, skincare, health and wellness, CPG, and more. Erica’s approach combines data-driven insights with creative vision, producing striking visuals, cohesive brand narratives, and innovative marketing strategies. Whether leading organic social strategy, providing creative strategy for high-converting paid social campaigns, or overseeing creative asset development, she brings a results-oriented approach to every project. Notable clients include: - Celebrity founded brand, The Little Market - RYZE Superfoods - Lemonade Insurance - Popdarts - AUSTERE Social Agency - Dose for Your Liver - Bambu Earth Skincare - Black Tulip Studio - Half Baked Harvest - Wine by Lamborghini - Thai Coco Areas of expertise include: - Creative Direction - Content Marketing & Social Media Strategy - Creative Strategy for Paid Ads - Lifestyle & Brand Photography - Email & SMS Marketing

  • Content Strategy
  • Social Media Management
  • Creative Direction
  • Digital Marketing
  • Creative Strategy
  • Email Marketing
  • Marketing
  • Brand Marketing
  • Social Media Strategy
  • Art Direction
  • Content Creation
  • Ecommerce
  • Photography
  • Blog Content
  • Graphic Design
Maaz S.

Chicago, Illinois

$65/hr
5.0
5 jobs

*(Rising talent on Upwork!) Need somebody that knows Meta Ads from the inside and out and can actually analyze and tell you whats wrong with your ad account in real time. Message me and Ill take a look at your ad account and tell you whats wrong then and there. Then we can make a plan to get a lower cpl and higher intent leads going into your pipeline. If you check my instagram @maazsiddiqii I do audits of local businesses all day there! My Experience… 👇 → Head Media Buyer at one of the top medical marketing agencies in the country. Managed $500K/month in ad spend across 35 client accounts, working directly with creative strategists to hit *profitable* cost per lead, not just cheap leads that never book Procedures I've marketed and sold through paid ads: - LASIK - Refractive Lens Exchange (RLE) - EVO ICL - Blepharoplasty (upper & lower — eyelids and under-eye bags) - Rhinoplasty - Plastic surgery & facial aesthetics → Currently managing paid ads for home service businesses Industries I'm running right now: - Outdoor lighting - HVAC - Garage door - Roofing → (1k Subs) Youtube @Maazsiddiqi and I should pop up 😀 Here's what I'll help you build. - CREATIVE STRATEGY — angles, hooks, scripts, testing unique and hot formats to reduce your CPA - MEDIA BUYING — Full Meta & TikTok ads management and setup - CRM Buildout - I will build out your entire CRM to make sure leads are properly followed up with and taken care of (Gohighlevel) If you're still reading this, let's work. Send me a message, and we can talk.

  • Digital Marketing
  • TikTok Ad
  • Lead Generation
  • Marketing
  • Facebook Ad Campaign
  • Google Ad Manager
  • Ecommerce
Jon R.

Chicago, Illinois

$95/hr
5.0
5 jobs

***TOP RATED freelancer for Brand Development, Strategy, Product Marketing*** Brand building is my specialty, and I am ready to help YOU build your business. I am a highly skilled brand development, marketing, product and content strategist with over 20 years of experience in the consumer products and retail industries. Clients include Target, Kraft, Bel Brands, Slimfast, Redbox, Fortune 500, non-profit and start-up firms. +Top 5% marketing consultants in Chicago, IL +Featured Speaker at RSW Agency & Branding Conference +Marketing panelist in Kellogg Marketing Conference As a marketing leader, I have professionally managed and worked on some of the largest consumer brands in the world, including Windex, Glade, Pledge, Optimum Nutrition, Amino Energy, Think Thin protein bars, Kraft Philadelphia cream cheese, Baby Bel and Laughing Cow Cheese, Slim Fast, Weight Watchers, and more. I have also helped start-up brands and small businesses reach their next level of sales, build brand equity, gain new customers, and maximize their full potential. In marketing leadership roles, I’ve developed powerhouse brand identities. go-to-market strategies, new product and innovation strategies, market research, consumer insights, annual marketing plans and more. And I am ready to do the same for you! As a freelancer, I have developed brand strategies and consulted for some of the leading Fortune 500 companies, multiple innovative brands, and fast-growing startups. Work has included category and market analysis, product research, competitive analysis, SWOT analysis, consumer research, go-to-market development, business model development, new product development, building operational and co-manufacture capability, and more. In addition to my professional experience, I have an MBA in Marketing, Strategy, and Entrepreneurship from the Kellogg School of Management at Northwestern University, a top business school. I am also a serial entrepreneur and have helped several Amazon and DTC E-commerce brands achieve sales and customer growth. I look forward to bringing my insights and expertise to your brand, new product launch, or development project!

  • Market Research
  • Product Development
  • Resume Writing
  • Brand Development
  • Financial Consulting
  • Brand Identity
  • Sales Analytics
  • Brand Management
  • Brand Consulting
  • Strategy
  • Branding
  • Management Consulting
  • Brand Strategy
  • Business Modeling
  • Career Coaching
Christina J.

Chicago, Illinois

$45/hr
4.7
7 jobs

Are you trying to build brand awareness, drive sales conversions, or generate content? The strategy behind each looks completely different, and that's where most influencer campaigns actually go wrong. That's the gap I fill. I'm CJ — a Creator Relations Manager and Creative Strategist who has been apart of campaigns for Google, Spotify, Airbnb, and Diageo. My work on Google's Black-Owned Friday reached 5.1M+ YouTube views and 500K+ social engagements — not because we found the biggest influencers, but because we built a creator strategy that actually fit the brand. I bring that same thinking to every client I work with, whether you're a startup figuring out your first creator program or an established brand whose influencer campaigns feel scattered and aren't converting. What I do: Creator & influencer strategy - Building creator programs that fit your brand positioning, not just your budget - Sourcing and vetting across nano to macro tiers with brand fit as the primary filter - UGC, gifting, seeding, affiliate programs, and product placement - Negotiating rate, deliverables, and usage rights directly with creators - Creates Briefs covering deliverables, FTC disclosure, content approvals, and exclusivity - Full campaign management and reporting that goes beyond vanity metrics - Comfortable working in CreatorIQ and Upfluence on top of my own systems Partnerships & business development - Identifying and approaching the right partners, collaborators, and talent - Building outreach systems and pipelines that convert - Relationship management with agencies and talent managers Industries: Wellness · Lifestyle · Beauty · Fashion · Tech · Consumer Goods If your influencer campaigns feel disconnected from your brand or you're building one from scratch and want to do it right the first time. I'd love to hear what you're working on.

  • Research & Strategy
  • Influencer Research
  • Influencer Marketing
  • Partnership & Collaborations Outreach
  • Outreach Strategy
  • Research & Development
  • Data Entry
  • List Building
  • Marketing
  • TikTok
  • Instagram
  • Grant Research & Prospect List

How it works

Post a job for freePost a job

Tell us what you need. Create your own job post or generate one with AI then filter talent matches.

Hire top talent fast

Consult, interview, and hire quickly, so you can meet the freelancers you're excited about.

Collaborate easily

Use Upwork to chat or video call, share files, and track project progress right from the app.

Payment simplified

Manage payments in one place with flexible billing options. Only pay for approved work, hourly or by milestone.

Don't just take our word for it

How do I hire a Digital Strategist near Chicago, IL on Upwork?

You can hire a Digital Strategist near Chicago, IL on Upwork in four simple steps:

  • Create a job post tailored to your Digital Strategist project scope. We’ll walk you through the process step by step.
  • Browse top Digital Strategist talent on Upwork and invite them to your project.
  • Once the proposals start flowing in, create a shortlist of top Digital Strategist profiles and interview.
  • Hire the right Digital Strategist for your project from Upwork, the world’s largest work marketplace.

At Upwork, we believe talent staffing should be easy.

How much does it cost to hire a Digital Strategist?

Rates charged by Digital Strategists on Upwork can vary with a number of factors including experience, location, and market conditions. See hourly rates for in-demand skills on Upwork.

Why hire a Digital Strategist near Chicago, IL on Upwork?

As the world’s work marketplace, we connect highly-skilled freelance Digital Strategists and businesses and help them build trusted, long-term relationships so they can achieve more together. Let us help you build the dream Digital Strategist team you need to succeed.

Can I hire a Digital Strategist near Chicago, IL within 24 hours on Upwork?

Depending on availability and the quality of your job post, it’s entirely possible to sign up for Upwork and receive Digital Strategist proposals within 24 hours of posting a job description.