Trust us…


you're gonna love it here.

Location: San Jose, California, USA (Hybrid) 

About Milestone: 

Milestone Inc. is a leading Digital Experience Software and Services company dedicated to providing comprehensive solutions across all touch points that enhance customer engagement and drive business growth. Milestone mission is to pioneer the distribution and visibility of content with an innovative platform that drives discovery, personalized experiences, and conversions powered by data and AI. We pride ourselves on our collaborative culture and commitment to excellence in everything we do and are certified Great Place to Work. 

About Role 

The Head of Marketing will lead the end-to-end marketing function for Milestone in close partnership with senior leadership, product, sales, customer success, and external ecosystem partners. The role is responsible for building and executing a high-impact marketing engine that strengthens brand visibility, drives thought leadership, supports product adoption, improves market positioning, and enables pipeline growth through events, partnerships, campaigns, content, and marketing operations. This is a strategic yet hands-on leadership role that requires strong execution discipline. The role will own key marketing programs including tradeshows and events, thought leadership operations, webinar and content programs, speaking engagements, industry partnerships, product marketing collateral, brand stewardship, and marketing platform governance including HubSpot and sales audit alignment. Strong Heads of Marketing in B2B SaaS are expected to connect strategy to measurable execution, align closely with sales and product teams, and run KPI-driven campaigns across content, events, and GTM motions 

Key Responsibilities 

Strategic Vision & Leadership 

• Define and lead an integrated marketing strategy that advances Milestone's brand positioning, thought leadership, product visibility, and commercial growth objectives 
• Partner closely with the executive team to translate company strategy into a focused marketing roadmap with clear priorities, outcomes, and resource allocation. 
• Serve as the steward of Milestone's market narrative, ensuring clarity, consistency, and differentiation across external channels and stakeholder touchpoints. 
• Build a performance-oriented marketing operating model that balances strategic brand building with measurable business impact. 
• Represent the voice of the market internally by bringing customer, partner, industry, and competitive insight into leadership decision-making. 
• Build and operationalize Milestone's thought leadership engine across webinars, articles, email campaigns, speaker applications, conference submissions, executive visibility, and content syndication 
• Build and operationalize a repeatable thought leadership engine spanning webinars, articles, executive communications, email campaigns, contributed content, and external speaking platforms. 

Operational Excellence & Scalable Growth  

• Own the planning and execution of trade shows, conferences, and external events, including sign-ups, sponsorship coordination, booth planning, logistics, materials, and post-event effectiveness tracking. 
• Ensure consistency and strength of Milestone brand positioning across website, presentations, logos, templates, messaging, bylines, and external brand representation 
• Lead the process for securing speaking engagements and visibility opportunities for senior leadership by identifying target platforms, managing submissions, and coordinating all supporting materials and follow-through. 
• Drive marketing partnership strategy and activation across industry associations, customer communities, media platforms, and ecosystem partners including HSMAI, Financial Brand, Choice, Leading, Preferred, Historic, and AI Hospitality Alliance. 
• Strengthen product marketing execution across one-pagers, solution collateral, product narratives, G2 presence, forum visibility, and SEO/GEO discoverability for Milestone products. 
• Establish strong governance over marketing systems and platforms, particularly HubSpot, campaign processes, reporting accuracy, data hygiene, and sales-marketing workflow alignment. 
• Build reporting frameworks and dashboards for marketing performance, campaign outcomes, event ROI, thought leadership reach, partnership impact, and brand visibility  
• Manage budgets, agencies, freelancers, and external vendors associated with marketing programs - Build scalable processes, calendars, templates, and governance mechanisms to improve execution quality and reduce dependency on ad hoc coordination 

 Customer-Centric Business Impact 

• Strengthen Milestone's reputation as a trusted authority in digital experience, search, visibility, and AI-driven marketing transformation for enterprise and multi-location brands. 
• Improve the quality and effectiveness of market-facing programs so that customers, partners, analysts, and prospects experience a more compelling and coherent Milestone story. 
• Ensure product and brand communications support customer confidence, market relevance, and stronger conversion across the buyer journey. 
• Create a stronger external presence for Milestone leadership and products in the forums, partnerships, and channels that matter most to target audiences. 
• Deliver measurable improvements in awareness, engagement, marketing contribution, and brand consistency.  

Cross-Functional Collaboration & Alignment 

• Work in close partnership with Sales to ensure campaigns, events, product narratives, and executive engagement programs contribute to pipeline development and account influence  
• Collaborate with Product and Services teams to ensure market-facing messaging, product positioning, and collateral accurately reflect customer value and strategic differentiation. 
• Partner with Customer Success and leadership teams to surface customer stories, proof points, and advocacy opportunities that strengthen thought leadership and product credibility. 
• Align with Design, Content, Digital, and Operations teams to ensure brand consistency and execution quality across all marketing assets and channels. 
• Manage external agencies, media partners, content contributors, event vendors, and ecosystem stakeholders with professionalism and outcome orientation. 

Innovation & High-Performance Culture 

• Build a modern, insight-led marketing function that uses data, experimentation, and market feedback to improve channel performance and message effectiveness 
• Encourage innovation in brand storytelling, content distribution, executive visibility, and digital engagement to keep Milestone ahead of category conventions. 
• Introduce scalable frameworks, templates, calendars, and governance mechanisms that improve speed, consistency, and quality of execution. 
• Build, coach, and inspire a capable marketing team with strong execution discipline, functional ownership, and a shared commitment to quality and impact. 
• Clarify roles, expectations, workflows, and success measures so that the team operates with focus, speed, and accountability. 
• Mentor team members in brand thinking, product marketing, event execution, content quality, and marketing operations rigor.  

Ideal Candidate Profile 

The ideal candidate is a sophisticated B2B marketing leader with the judgment to shape strategy and the operational depth to ensure disciplined execution. You are equally comfortable refining market positioning, building senior executive visibility, reviewing a product one-pager, evaluating an event sponsorship, improving HubSpot governance, or driving a webinar and content plan to completion. You understand how modern SaaS marketing must connect brand, product narrative, ecosystem credibility, and revenue enablement into one integrated system. You bring executive presence, high standards, and a strong bias toward action. You are known for building clarity in ambiguous environments, strengthening cross-functional trust, and creating momentum where functions have historically operated in silos. You care deeply about quality, relevance, and market perception, and you have the maturity to lead through influence, data, and consistency rather than noise 

Required Experience & Qualifications: 

• 12+ years of progressive marketing experience, with substantial leadership experience in B2B SaaS, digital platforms, enterprise technology, or martech environments 
• Proven success leading integrated marketing functions spanning brand, thought leadership, product marketing, partnerships, campaigns, and marketing operations 
• Strong experience managing trade shows, conferences, executive speaking opportunities, and strategic partnership programs. 
• Demonstrated capability in building thought leadership programs across webinars, articles, outbound communications, and executive content platforms. 
• Deep familiarity with product marketing fundamentals including messaging, collateral, competitive positioning, review platforms, and market-facing product storytelling. 
• Hands-on experience with marketing technology platforms, especially HubSpot, campaign operations, lead management workflows, and performance reporting. 
• Strong executive communication skills with the ability to influence senior leaders, external partners, and cross-functional stakeholders. 
• Strong analytical and business acumen; ability to define KPIs, assess ROI, and drive marketing decisions using data and market insight. 
• Experience leading and developing high-performing teams in growth-oriented, fast-paced organizations. 
• Bachelor's degree required; MBA or advanced degree in Marketing, Business, Communications, or related field preferred. 

Key Focus Areas 

• Brand positioning and category authority. 
• Thought leadership strategy and executive visibility. 
• Trade shows, conferences, and event effectiveness. 
• Strategic industry partnerships and ecosystem engagement. 
• Product marketing and sales enablement collateral. 
• Website, templates, logos, and brand governance. 
• HubSpot operations, campaign discipline, and reporting rigor. 
• Cross-functional GTM alignment and measurable business impact. 

What We Offer 

• Competitive salary and performance-based incentives. 
• Comprehensive benefits package. 
• Opportunity to work in a collaborative and innovative environment. 
• Career growth and professional development opportunities. 
• A chance to be part of a global team that makes a significant impact in the industry. 
• How to Apply 

Interested candidates are invited to submit their resume and a cover letter outlining their qualifications and vision for the role plus previous experience align with key attributes, responsibilities, clear wins or learnings. 

Why Milestone 

Founder Led, Award Winning Platform, Great Place to Work, Engaging Culture.