Keith Kostrzewski

Keith Kostrzewski Email and Phone Number

Revenue & Commercial Strategy Executive | Expert in GTM Operations, Sales Transformation, & Revenue Growth | open to full-time and consulting engagements @ sideKick Group
Keith Kostrzewski's Location
Hilton Head Island, South Carolina, United States, United States
About Keith Kostrzewski

I’m a strategic and collaborative leader who thrives on turning complex challenges into transformative opportunities. With two decades of experience in driving growth and operational excellence across B2B, software/SaaS, and EdTech, I partner with executive teams to build high-performing organizations through data-driven decision-making, scalable processes, and continuous improvement.I believe in empowering teams to achieve sustainable growth by aligning strategy with execution, leveraging data for insights, and fostering a culture of accountability and innovation. My approach centers on creating clarity amidst complexity, setting ambitious goals, and designing strategies that scale.My Expertise Includes:- Strategic Planning & Execution: Designing and executing go-to-market strategies that expand market presence, exceed revenue targets, and drive long-term success.- Operational Excellence: Implementing scalable processes and systems that boost organizational efficiency, reduce costs, and enable seamless cross-functional collaboration.- Revenue Operations: Leveraging analytics and repeatable processes to optimize performance across sales, marketing, and customer success.- Financial Acumen: Utilizing financial modeling and data-driven insights to support decision-making and optimize resource allocation.- Sales Leadership: Building and leading high-performing teams through coaching, skill development, and fostering a culture of continuous learning and growth.My Approach:- Align business operations and GTM strategies to maximize impact and drive sustainable growth.- Transform data into actionable insights, enabling informed decisions and accurate forecasting.- Cultivate a collaborative and results-oriented culture, inspiring teams to exceed expectations.- Lead change management initiatives that support innovation and accelerate business transformation.My goal is to help organizations unlock their full potential by driving strategic growth, optimizing revenue operations, and empowering teams to perform at their highest level. With a combination of strategic vision, operational expertise, and financial acumen, I turn inefficiencies into growth drivers and ideas into actionable strategies that deliver tangible results.Let’s connect if you’re looking for a strategic leader who can spearhead complex initiatives, optimize revenue operations, and inspire teams to achieve more.

Keith Kostrzewski's Current Company Details
sideKick Group

Sidekick Group

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Revenue & Commercial Strategy Executive | Expert in GTM Operations, Sales Transformation, & Revenue Growth | open to full-time and consulting engagements
Keith Kostrzewski Work Experience Details
  • Sidekick Group
    Founder, Chief Revenue And Sales Strategy Executive
    Sidekick Group Jan 2021 - Present
    Hilton Head Island, South Carolina, Us
    Lead a consultancy specializing in strategic go-to-market (GTM) planning, sales transformation, and revenue operations optimization for B2B and SaaS organizations. Partner with executive teams to develop and execute growth strategies that enhance revenue performance, improve sales efficiency, and achieve sustainable business outcomes.• Go-to-Market Strategy & Execution: Architect and implement GTM strategies that integrate Sales, Marketing, and Customer Success functions to drive market penetration, accelerate revenue growth, and achieve competitive advantage.• Revenue Operations Optimization: Streamline lead-to-cash processes by optimizing CRM systems, territory planning, and incentive structures, resulting in improved forecast accuracy, sales productivity, and overall revenue performance.• Sales Leadership & Enablement: Design and deploy high-impact sales enablement programs and performance management frameworks (e.g., MEDDIC, Challenger Sale, SPIN Selling) to build high-performing teams and elevate sales outcomes.• Executive-Level Strategic Advisory: Provide strategic advisory and leadership to executive teams, leading initiatives that deliver double-digit revenue growth, operational excellence, and cross-functional alignment.Partner with clients across industries such as education, healthcare, commercial real estate, sports and entertainment, and technology to transform GTM strategy and revenue operations, achieving measurable growth and maximizing ROI.
  • Abode Development
    Co-Founder & Chief Business Officer
    Abode Development Jul 2024 - Present
    Abode Development was founded with a mission to create high-quality, multi-family residential properties that strengthen the communities we love, starting with Hilton Head, SC. Our focus is on workforce housing solutions that address the critical needs of the Lowcountry's essential workforce, ensuring that the people who sustain our vibrant region can live and thrive where they work.As co-founder, I lead business operations, community partnerships, investor relations, and external development efforts. At Abode Development, we believe in building more than housing—we build opportunities, connections, and a foundation for a stronger community. By collaborating with frontline workers, service industry organizations, and local leaders, we aim to create sustainable housing solutions that benefit all residents while preserving the unique character of the Lowcountry.
  • Oncore Golf
    Advisor, Growth Strategy
    Oncore Golf Jan 2021 - Present
    Buffalo, New York, Us
  • Carnegie Learning
    Vice President Of Revenue Operations
    Carnegie Learning Dec 2022 - Jul 2023
    Pittsburgh, Pa, Us
    • Led revenue operations strategy development and execution, aligning go-to-market initiatives company-wide with comprehensive performance insights, enabling data-driven decision-making across the organization.• Executed a comprehensive sales effectiveness program, including data-driven territory optimization, bespoke account-based selling models, enhanced Salesforce-based performance management and forecasting, and redesigned incentive compensation plans
  • Pi-Top
    Global Vice President Of Sales And Revenue Operations
    Pi-Top Apr 2021 - Dec 2022
    London, Select State, Gb
    • Led the transformation of company strategy from retail to B2B education market, overhauling the go-to-market function under extreme budget and capacity constraints.• Drove 83% year-over-year and triple-digit growth over three quarters with only 25% of the prior year's sales team size, by restructuring sales processes, enhancing technology utilization, and refocusing on the Ideal Customer Profile for the education market. • Orchestrated a comprehensive tech stack overhaul (CRM, ERP, e-Commerce) and restructured channel sales partnerships, improving workflow efficiency and unlocking $1M in working capital for strategic reinvestment, resulting in increased operational capacity and improved supply chain performance.
  • Curriki
    Chief Executive Officer
    Curriki Nov 2019 - Jan 2021
    Cupertino, California, Us
    Spearheaded a strategic transformation, transitioning the organization to a SaaS model and launching an award-winning open-source platform. Position impacted by Covid-19.• Achieved a 3x increase in user engagement and expanded the partner ecosystem by nearly 10x.• Developed and executed a data-driven growth strategy, generating over $3M in sales pipeline within the first year and securing $6M in funding from prominent investors, resulting in 40% growth in the first year.• Navigated the organization through the COVID-19 pandemic, adapting go-to-market strategies and operations to ensure business continuity and drive growth.
  • Lego Education
    Head Of Enterprise Sales, North America
    Lego Education Sep 2017 - Nov 2019
    Billund, Dk
    Led strategic sales transformation in U.S., with extensive market analysis and segmentation to identify Ideal Customer Profile, Enterprise buyer personas, and inform go-to-market strategies.• Implemented targeted sales plays and bespoke account-based initiatives, resulting in a 25% increase in K-12 Education market revenue and a 130% increase in enterprise sales.• Led a successful transition from a channel-centric to a direct sales model, optimizing sales quotas, incentives, and enablement resources, achieving a 20% increase in sales productivity and customer acquisition.• Built and led a high-performing sales team, fostering a culture of data-driven decision-making and continuous improvement. Implemented a sales performance management system and collaborated with marketing, customer success, and product teams to optimize the end-to-end customer journey.• Core member of global sales innovation committee, aligning sales strategies with organizational goals across pricing, services, and product development.
  • Discovery Communications
    Director, Enterprise Partnerships
    Discovery Communications Jan 2016 - Sep 2017
    New York, Us
    • Established and grew strategic partnerships: Developed and maintained relationships with executives and project teams of large, strategic customers, including Miami-Dade, Santa Rosa, Collier County, and Orange County, ensuring alignment with overarching goals and driving satisfaction and retention.• Expanded Enterprise Partner segment: Identified key objectives and growth opportunities for high-value clients, resulting in significant segment growth and enhanced relationships with major districts.• Implemented strategic account planning: Created a corporate framework for cross-functional strategic account planning processes to enhance collaboration and operational efficiency
  • Thinkcerca
    Vice President Customer Operations
    Thinkcerca Mar 2015 - Jan 2016
    Chicago, Illinois, Us
    Lead and manage the Customer Success team, setting strategic direction and objectives to enhance customer satisfaction and retention.• Collaborate with Sales and Product teams to identify opportunities for growth and expansion within existing customer accounts.• Support presales activities by developing relationships with key stakeholders, understanding customer requirements, and crafting compelling proposals and solutions.
  • Pearson North America
    Account General Manager (Large Accounts)
    Pearson North America Jun 2012 - Jul 2014
    London, Gb
    Transitioned to Pearson through the acquisition of SchoolNet, leading post-merger integration and overseeing key accounts across multiple business units.· Spearheaded client portfolio expansion and optimization, leveraging data-driven insights to drive 25% account revenue growth and 20% improvement in client retention.· Led strategic initiatives to optimize P&L performance, including pricing, product bundling, and operational efficiency· Developed an account health monitoring system, proactively identifying risks and opportunities to enhance the client experience.
  • Schoolnet
    Enterprise Client Partner (Program Lead)
    Schoolnet Jan 2009 - Jun 2012
    New York, New York, Us
    In this role, I was accountable for strategic planning, project management, and client relationship management, leading enterprise deployments for large-scale Instructional Management Systems and online assessment platforms. • Senior Client lead for largest customers, responsible for profitable growth, customer satisfaction, program oversight and P&L.• Built strong executive business relationships with clients, identifying opportunities needing strategy, insights, tracking, or analytics. • Served on strategic Transition team during acquisition by Pearson, building customer and operational best practices.
  • Schoolnet
    Head Of Revenue Operations And Sales Enablement
    Schoolnet Sep 2004 - Dec 2008
    New York, New York, Us
    • Transformed sales operations by implementing advanced pipeline management, sales enablement, and pricing strategies, driving a 30% increase in sales productivity and 20% improvement in forecast accuracy.• Collaborated with executive leadership to execute data-driven sales initiatives, leading cross-functional projects including account planning, incentive plan development, and product training• Led the implementation of Microsoft Dynamics CRM and the Complex Sale methodology, driving adoption and optimizing sales processes to improve efficiency and effectiveness.
  • Classwell Learning Group, Inc. (A Part Of Houghton Mifflin)
    Manager Of Sales Operations
    Classwell Learning Group, Inc. (A Part Of Houghton Mifflin) Jun 2000 - Jul 2003
  • Buffalo Bills
    Graduate Assistant: Gameday Operations And Sponsorship Activation
    Buffalo Bills May 1999 - Jan 2000
    Orchard Park, Ny, Us
    Oversaw game day preparations, on-field production setup, quality control checks, and maintenance tasks in collaboration with Corporate Partnerships, Premium Seating, and Ticket Office. Developed operations manual and processes for issue resolution and employee reward system.• Launched Guest Experience Program: Recruited, trained, and managed a team of 50 part-time staff dedicated to enhancing the game-day experience following a major stadium renovation. Manage the Gameday Guest Services team to improve customer satisfaction and operational efficiency.• Supported event marketing: Assisted in sponsorship activation and partner experience initiatives, ensuring seamless integration and execution of event marketing strategies.

Keith Kostrzewski Skills

Strategic Partnerships Crm Cross Functional Team Leadership Leadership Strategy Management Strategic Planning Enterprise Software Account Management Program Management Marketing Strategy Marketing Sales Project Management Business Development Sales Operations Team Building Analysis Forecasting Process Improvement Sales Management Scope Management Sales Process Public Speaking New Business Development Salesforce.com Business Strategy Change Management Saas Product Marketing Client Relationship Building Client Engagement Enterprise Collaboration Internal Communications Fundraising Entrepreneurship Solution Selling Team Leadership Start Ups Technology Adoption Collaborative Planning Operations Management Sales Presentations Executive Management Business Alliances Product Management Consulting Competitive Analysis Analytics Social Media

Keith Kostrzewski Education Details

  • Northwestern University - Kellogg School Of Management
    Northwestern University - Kellogg School Of Management
    General
  • Providence College
    Providence College
    Marketing
  • Canisius High School
    Canisius High School
  • Providence College
    Providence College
    General

Frequently Asked Questions about Keith Kostrzewski

What company does Keith Kostrzewski work for?

Keith Kostrzewski works for Sidekick Group

What is Keith Kostrzewski's role at the current company?

Keith Kostrzewski's current role is Revenue & Commercial Strategy Executive | Expert in GTM Operations, Sales Transformation, & Revenue Growth | open to full-time and consulting engagements.

What is Keith Kostrzewski's email address?

Keith Kostrzewski's email address is kd****@****hoo.com

What is Keith Kostrzewski's direct phone number?

Keith Kostrzewski's direct phone number is +191742*****

What schools did Keith Kostrzewski attend?

Keith Kostrzewski attended Northwestern University - Kellogg School Of Management, Providence College, Canisius High School, Providence College.

What are some of Keith Kostrzewski's interests?

Keith Kostrzewski has interest in American Soccer, New York City, Dunkin' Donuts, Friday Night Lights (Tv Series), Childrens Charities, Kellogg School Of Management, The Sopranos (Tv Series), Gizmodo, Jack Johnson, Coldplay (Band).

What skills is Keith Kostrzewski known for?

Keith Kostrzewski has skills like Strategic Partnerships, Crm, Cross Functional Team Leadership, Leadership, Strategy, Management, Strategic Planning, Enterprise Software, Account Management, Program Management, Marketing Strategy, Marketing.

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