Digital Marketing Sales Manager

Rick Bastian

Lisle, IL 815-***-**** ️ ***********@*****.*** linkedin.com/in/rickbastian EXECUTIVE SUMMARY

Proven sales leader with 15+ years of experience building and scaling SMB-focused sales teams across tech, SaaS, and digital marketing. Expert at leading frontline sales reps, developing KPI-driven coaching models, and driving strong pipeline health and conversion. Successfully managed remote and hybrid teams in high-volume environments, including distributed markets across North America. Highly skilled at operationalizing GTM strategy, enhancing rep performance, and using AI tools (Fireflies, Notion, ChatGPT) to streamline forecasting, reporting, and outreach.

EXPERIENCE

Groupon

Regional Sales Manager – Local Sales (US & Canada)

Chicago, IL 11/2024 – Present

● Lead 70+ sales professionals across Business Development and Merchant Development, driving SMB merchant acquisition and retention across verticals such as Health & Beauty, Food & Drink, and Entertainment.

● Drove a 300%+ increase in Gross Profit in Chicago within 6 months through full GTM overhaul and launch of “The Chicago Project.”

● Introduced structured coaching, rep KPIs, real-time dashboards, and sales enablement workflows—boosting productivity by 45% and reducing ramp time.

● Championed performance-based culture with strong accountability, pipeline hygiene, and cadence-based coaching across distributed teams.

● Launched and scaled BD/MD Agency Model across North America, reviving dormant SMB accounts and increasing rep activation and conversion. Uber for Business

Head of SMB Sales – US & Canada

Chicago, IL 03/2020 – 03/2022

● Employee #1 for Uber’s SMB sales organization; built team of 60+ reps, managers, and directors across U.S., Brazil, and the Philippines.

● Drove YoY growth from $13M to $24M while implementing core KPIs, SOPs, and lifetime-value-based sales targeting.

● Led daily standups, 1:1 rep coaching, and weekly pipeline reviews to track top-of-funnel inputs and close rates across verticals (hospitality, auto, professional services).

● Oversaw implementation of Salesforce and automated reporting systems to manage productivity, forecasting, and pipeline stage velocity. Yelp

Senior Sales Manager

Chicago, IL 04/2018 – 09/2019

● Managed 20 sales reps and 2 team leads selling digital solutions to local SMBs.

● Exceeded quota for 14 consecutive months, achieving $10M+ in revenue.

● Rated #1 sales manager in Chicago office and won President’s Club Top 1% among 600+ peers nationwide.

● Led DEI mentorship program that increased manager diversity from 5% to 35%. Yext

Enterprise Account Executive

Chicago, IL 09/2016 – 11/2017

● Closed 3-year SaaS deals ($100K–$500K) with national brands including Little Caesars and Redwing Shoes.

● Focused on SMB franchise networks and regional rollouts of search optimization software.

UpCity

Director, Partnerships & Business Development

Chicago, IL 02/2015 – 08/2016

● Built and led inside sales team of 13+ reps targeting SMB digital marketing needs.

● Exceeded sales targets by 250% and established key partnerships with WordStream and HubSpot.

DexYP (formerly Yellow Pages)

Director, Premium Digital Services

Chicago, IL 05/2005 – 02/2015

● Managed 200+ digital sales professionals nationally focused on small business solutions.

● Grew the digital ad sales channel into a $20M revenue stream within 18 months.

● Promoted rapidly from Account Executive to Director and led digital transformation of legacy business.

EDUCATION & TRAINING

University of Wisconsin – Madison

● Bachelor’s Degree – Consumer Affairs in Business 2005 Certifications & Ongoing Learning:

● HarvardX: AI Implementation for Business (in progress)

● Sales Enablement Strategy – Sales Assembly

● B2B Sales Strategy – Reforge

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