Head of Sales Operations and Enablement

Head of Sales Operations and Enablement


United States, Santa Clara – CA

This is a Full Time, Exempt position based in our Santa Clara, CA office in the San Francisco – Bay Area. This position reports to the Chief Revenue Officer of the Company. 

It will be required to report to the Santa Clara, CA office during the implementation of CPQ and the integration of Billing into Salesforce.com.

Your mission

Are you interested in joining a SaaS company whose cloud software is used to manage the digital commerce storefront infrastructure for thousands of merchants globally? Do you enjoy being an integral part of a sales leadership team, helping to grow the revenue and team dramatically? Do you like expanding the Salesforce.com stack and taking the lead in driving the addition of CPQ and Billing?

Webscale is a leading managed services platform. Its fully optimized, highly secure, and reliable automation platform streamlines the migration and management of ecommerce storefronts in any public cloud, including Amazon Web Services, Google Cloud Platform, and Microsoft Azure.

As we extend our business, we are looking for a Head of Sales Operations and Enablement to lead and continue to build our global sales team.

What we’re looking for in you

We have aggressive plans for continued expansion with thousands of customers and growing. As a Head of Sales Operations and Enablement at Webscale, you will draw upon your solid analytical, critical thinking, and problem-solving skills to create a more robust onboarding program, optimize processes to increase sales efficiency, and remove friction.

What you’ll be doing

The role requires business maturity and in-depth knowledge of the sales cycle and operations. Developing close working relationships with internal and external stakeholders to ensure the sales and services organization’s efficient operation and success is a must.

  • Design, implement, and manage sales forecasting, planning, and budgeting processes. Establish high levels of quality, accuracy, and process consistency in the sales and services organization’s planning, forecasting, and budgeting approaches.
  • Ensure planning, forecasting, and budgeting efforts are appropriately integrated with other planning processes employed within the firm.
  • Act as a trusted advisor to Sales and Marketing leaders, leveraging data and analyses to land business insights, develop GTM strategies, and scale the business.
  • Play an active leadership role in the Deal Desk to review, approve and help structure complex deals.
  • Work closely with the Finance team to ensure all booking activity is reported correctly to finance to support financial reporting requirements.
  • Provide leadership to the sales organization and counsel to the MD WW Sales and Services in implementing sales/services organization objectives that appropriately reflect the firm’s business goals.
  • Responsible for working with the Sales leadership team to equitably assign sales team quotas and ensure the firm’s financial objectives are optimally allocated to all sales channels and resources through the quota program. 
  • Be accountable for the timely assignment of all sales and services organization objectives, and partner with senior sales leadership to identify opportunities for process improvement.
  • Facilitate successful implementation of new programs through the revenue organization by ensuring a well-defined, efficient process is in place for launch.
  • Foster an organization of continuous process improvement. 
  • Work with Sales and Services leadership on recommendations for changing roles, coverage models, or team configurations to maximize revenue productivity.
  • Lead a change management process to build organizational understanding of proposed changes, establish support from key leadership stakeholders, and implement new deployment and job models effectively.
  • Work with Human Resources and senior sales leadership, assist in designing sales incentive compensation programs that provide market-competitive pay, reinforce sales organization strategy, and align with business and sales organization objectives.
  • Work closely with Accounting, Finance, and Human Resources to establish rules, policies, and procedures associated with sales and services compensation.
  • Assist sales and services management in understanding process bottlenecks and inconsistencies. 
  • Work with Sales, Services, Pre-sales, Customer Success, and Marketing to ensure we apply best practices in all aspects of the Sales/Revenue Ops function.
  • Participate in the Annual (and ongoing) Sales and Services Management strategic planning process in support of hitting annual sales objectives.
  • Design and implement a Sales Playbook consisting of all relevant content, sales and services best practices, process training materials, and a public repository of all appropriate documentation.
  • Analyze sales processes and mechanisms for sub-optimal performance, focusing on defect reduction and productivity. Communicate findings clearly and effectively and make recommendations for improvement.
  • Identify reporting issues, and gaps in processes, and drive timely resolution.
  • Conduct sophisticated and creative analysis of complex data and translate the results into actionable deliverables, messages, and presentations.
  • Work closely with sales leadership and Human Resources to establish a sales team training plan focused on developing and reinforcing critical sales competencies. Prioritize training objectives for selling, sales management, services professionals, and sales/services support roles.
  • Develop a Competency Certification program for all sales personnel within an LMS solution.
  • Oversee the delivery of field training to sales, partner management, and sales leadership personnel.
  • Coordinate training delivery to sales, sales management, and sales support personnel in managing initial onboarding and ongoing development.
  • Manage and maintain all of the knowledge management resources for the sales team (Sales Playbook, Training resources, RFP data library) and look for ways to innovate around process improvement continuously.
  • Build and manage the knowledge management resources of the revenue team, including onboarding and ongoing training, including Industry, Product, Process, and Skills training.

Reporting Analytics and Technology Enablement

  • Work closely with senior revenue leadership to define the optimal performance measurements and performance management programs required to ensure sales/services organization success.
  • Align reporting, training, and incentive programs with these performance management priorities.
  • Establish best practices and processes for calculating and reporting variable incentive plans for all sales and services team members. This includes the ongoing reporting and analysis of performance against objectives such as quota, commission reporting, pipeline creation, forecasting, staffing metrics, employee churn, ramp-up, onboarding, utilization, billing rates, pricing metrics, LTV, client churn, client satisfaction, etc. 
  • Ensure sales and services reports and other internal intelligence is provided to the sales organization. Develops new reporting tools as needed. Coordinates with sales leadership and other stakeholders to lead efficient and accurate sales force reporting initiatives.
  • Oversee sales compensation plan administration, sales compensation program rules, policies, and procedures.
  • Responsible for efficiently allocating technology, support, and training resources impacting the revenue organization. Accountable for accurate and on-time reporting essential for revenue organization effectiveness.  
  • Monitor the accuracy and distribution of sales reports and other intelligence essential to the revenue organization. Recommend revisions and assist in the development of new reporting tools as needed.
  • Leverage enabling technologies, including SF.com/Pardot, to support field sales teams. Monitor compliance with standards for maintaining CRM data. Work to optimize the effectiveness of technology investments.
  • Lead the implementation of SF.com CPQ & Billing

What you should have

  • The ideal candidate has extensive experience managing, implementing, and fine-tuning Salesforce.com CRM, Pardot, CPQ, and Billing.
  • Driven: You are a driven team player, collaborator, and relationship builder whose infectious can-do attitude inspires others and encourages excellent performance in a fast-moving environment.
  • Entrepreneurial: You thrive in a fast-paced, changing environment, and you’re excited by the chance to play a significant role.
  • Relentless Improvement: We are growing our team and building our company. Ideal candidates will be enthusiastic seekers of new ideas for improvement and will be excited to stay current in the practices of other top startups. We want you to bring your thoughts, constantly hatch new ideas and share recommendations often. We have a high bar and will always look to raise it.
  • Passionate: You must be passionate about technology and ensuring our clients are successful; we love seeing hunger and ambition.

Standard Qualifications and Experience for a Senior Director Role reporting to the CRO

  • 10+ years of success leading sales operations and enablement in a fast-paced, dynamic software sales environment
  • Must have an ability to work independently as well as on a team in a collaborative environment and have an excellent understanding of Sales Operations requirements and strategic selling environments
  • Must possess strong time management skills and understand sales operations role, pipeline management, CRM, and forecasting principles
  • Have excellent written and verbal communication and presentation skills in managing all aspects of sales operations and revenue management.
  • Sales process knowledge and previous experience working with sales onboarding, enablement and  
  • Strong commercial awareness, excellent interpersonal skills
  • Advanced computer skills: Microsoft Word, Excel, PowerPoint, G-suite, SF.com, CPQ, Pardot, Outreach, LinkedIn Sales Navigator

About Webscale

Webscale is a leading managed services platform. Its fully optimized, highly secure, and reliable automation platform streamlines the migration and management of ecommerce storefronts in any public cloud, including Amazon Web Services, Google Cloud Platform, and Microsoft Azure.

Webscale powers Fortune 1000 brands and thousands of other B2C, B2B, and B2E ecommerce storefronts across 12 countries and has offices in Santa Clara, CA; Boulder, CO; San Antonio, TX; Bangalore, India; and London, UK.

Follow this link to apply via LinkedIn.