Keith Kostrzewski
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Keith Kostrzewski Email & Phone Number

Revenue & Commercial Strategy Executive | Expert in GTM Operations, Sales Transformation, & Revenue Growth | open to full-time and consulting engagements at sideKick Group
Location: Hilton Head Island, South Carolina, United States 14 work roles 4 schools
1 work email found @pi-top.com 7 phones found area 917, 617, 716, 212, and 860 LinkedIn matched
✓ Verified May 2026 4 data sources Profile completeness 100%

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Current company
Role
Revenue & Commercial Strategy Executive | Expert in GTM Operations, Sales Transformation, & Revenue Growth | open to full-time and consulting engagements
Location
Hilton Head Island, South Carolina, United States

Who is Keith Kostrzewski? Overview

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Quick answer

Keith Kostrzewski is listed as Revenue & Commercial Strategy Executive | Expert in GTM Operations, Sales Transformation, & Revenue Growth | open to full-time and consulting engagements at sideKick Group, based in Hilton Head Island, South Carolina, United States. AeroLeads shows a work email signal at pi-top.com, phone signal with area code 917, 617, 716, 212, 860, and a matched LinkedIn profile for Keith Kostrzewski.

Keith Kostrzewski previously worked as Founder, Chief Revenue and Sales Strategy Executive at Sidekick Group and Co-Founder & Chief Business Officer at Abode Development. Keith Kostrzewski holds Master Of Business Administration (M.B.A.), Business Administration And Management, General from Northwestern University - Kellogg School Of Management.

Company email context

Email format at sideKick Group

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{first}@pi-top.com
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Profile bio

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.

Listed skills include Strategic Partnerships, Crm, Cross Functional Team Leadership, Leadership, and 46 others.

Current workplace

Keith Kostrzewski's current company

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sideKick Group
Sidekick Group
Revenue & Commercial Strategy Executive | Expert in GTM Operations, Sales Transformation, & Revenue Growth | open to full-time and consulting engagements
AeroLeads page
14 roles

Keith Kostrzewski work experience

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Founder, Chief Revenue And Sales Strategy Executive

Current

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.
  • 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.
  • 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.
  • 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.
  • 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.
Jan 2021 - Present

Co-Founder & Chief Business Officer

Current

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.

Jul 2024 - Present

Advisor, Growth Strategy

Current

Buffalo, New York, US

Jan 2021 - Present

Vice President Of Revenue Operations

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.
Dec 2022 - Jul 2023

Global Vice President Of Sales And Revenue Operations

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.
  • 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.
Apr 2021 - Dec 2022

Chief Executive Officer

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.
Nov 2019 - Jan 2021

Head Of Enterprise Sales, North America

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.
  • Core member of global sales innovation committee, aligning sales strategies with organizational goals across pricing, services, and product development.
Sep 2017 - Nov 2019

Director, Enterprise Partnerships

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.
  • 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
Jan 2016 - Sep 2017

Vice President Customer Operations

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.
Mar 2015 - Jan 2016

Account General Manager (Large Accounts)

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.

Jun 2012 - Jul 2014

Enterprise Client Partner (Program Lead)

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.
  • 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.
Jan 2009 - Jun 2012

Head Of Revenue Operations And Sales Enablement

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.
Sep 2004 - Dec 2008

Manager Of Sales Operations

Classwell Learning Group, Inc. (A Part Of Houghton Mifflin)
Jun 2000 - Jul 2003

Graduate Assistant: Gameday Operations And Sponsorship Activation

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.
  • 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.
  • Supported event marketing: Assisted in sponsorship activation and partner experience initiatives, ensuring seamless integration and execution of event marketing strategies.
May 1999 - Jan 2000
4 education records

Keith Kostrzewski education

Master Of Business Administration (M.B.A.), Business Administration And Management, General

Northwestern University - Kellogg School Of Management

Bs, Marketing

Providence College

Education record

Canisius High School

Bachelor Of Business Administration - Bba, Marketing/Marketing Management, General

Providence College
FAQ

Frequently asked questions about Keith Kostrzewski

Quick answers generated from the profile data available on this page.

What company does Keith Kostrzewski work for?

Keith Kostrzewski works for sideKick Group.

What is Keith Kostrzewski's role at sideKick Group?

Keith Kostrzewski is listed as Revenue & Commercial Strategy Executive | Expert in GTM Operations, Sales Transformation, & Revenue Growth | open to full-time and consulting engagements at sideKick Group.

What is Keith Kostrzewski's email address?

AeroLeads has found 1 work email signal at @pi-top.com for Keith Kostrzewski at sideKick Group.

What is Keith Kostrzewski's phone number?

AeroLeads has found 7 phone signal(s) with area code 917, 617, 716, 212, 860 for Keith Kostrzewski at sideKick Group.

Where is Keith Kostrzewski based?

Keith Kostrzewski is based in Hilton Head Island, South Carolina, United States while working with sideKick Group.

What companies has Keith Kostrzewski worked for?

Keith Kostrzewski has worked for Sidekick Group, Abode Development, Oncore Golf, Carnegie Learning, and Pi-Top.

How can I contact Keith Kostrzewski?

You can use AeroLeads to view verified contact signals for Keith Kostrzewski at sideKick Group, including work email, phone, and LinkedIn data when available.

What schools did Keith Kostrzewski attend?

Keith Kostrzewski holds Master Of Business Administration (M.B.A.), Business Administration And Management, General from Northwestern University - Kellogg School Of Management.

What skills is Keith Kostrzewski known for?

Keith Kostrzewski is listed with skills including Strategic Partnerships, Crm, Cross Functional Team Leadership, Leadership, Strategy, Management, Strategic Planning, and Enterprise Software.

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