Head of Sales Enablement

This job posting expired and applications are no longer accepted.
Paddle Published: November 6, 2020
London, United Kingdom
Job Type


Paddle is one of the fastest growing SaaS businesses in the world, and certainly in the UK. We've got ambitions to be the platform which every single successful SaaS business in the world is using to run and grow their business.

As the SaaS space expands there's more potential than ever to build a huge software company. Yet, having a great product is only part of the journey. Too often a business will fail, or have their growth stunted by the operational burden of selling their product.

For all, too much time and money is wasted trying to handle payments, recurring billing, tax, fraud, invoicing, and more.

Moreover with the right commerce infrastructure and setup; growth can be accelerated. All of Salesforce, HubSpot, Intercom, and other stalwarts of the SaaS world have something in common. They have products which are sold to buyers big and small, all over the world, and are obsessed with constant optimisation. We are part of this environment.

Paddle gives all SaaS companies this best-in-class infrastructure from day one. We provide a single platform which handles checkout, billing, taxes, fraud, currencies, language, payment methods and more. Allowing all sellers to sell how they want, to who they want.

Meanwhile, best-in-class suggestions are served up to sellers helping them optimise their own go-to-market. From hyper-local pricing suggestions, to identifying opportunities to expand a customer account.

Working with C-level executives at some of the fastest growing SaaS companies in the world, and even influencing their go-to-market strategy, has fuelled our extraordinary growth. Our sales team has grown from 5 to 30 over the past year, and is further expanding in the UK and the US. This presents an incredible challenge and that is where you come in!

We are looking for a smart, ambitious and autonomous specialist – with SaaS experience – to:

  • Lead the creation and deployment of all sales on-boarding, training and ongoing development, leading to consistent quota achievement for the team.
  • Be the central point of contact for sales enablement and work closely with Product Marketing on educating the sales team on Paddle.
  • Be able to identify key business insights from your deep visibility to sales activity, therefore help Product Marketing craft impactful go-to-market strategies and initiatives .

All of this at scale, and in a world where our market and therefore our messaging and sales approach are constantly adapting to the pace of ongoing change.

In addition, sales enablement at Paddle is more than building the sales playbook and coaching managers and reps towards it. Our sales, marketing, and commercial ops team are very data-driven and tech heavy.

We capture and synthesise data from dozens of different sources to direct our account targeting and segmentation, personalise our messaging and templating, and trigger the right sales outreach, tasks, and sequences at the right time. Sales side, we use Outreach.io, Salesforce, and shortly a live chat tool integrated deeply with Clearbit, Hull, and our own "software universe" database.

What you'll do

  • Work closely with sales leadership, marketing and commercial ops to iterate over our approach – messaging, the tools, the outreach program etc.
  • Understand the platform and technology we provide and be able to fully articulate this to all members of the team – both technical and non-technical.
  • Derive insights from sales calls, emails and other touch-points to help drive improved response rates and win rates.
  • Teach and improve the team on how to position Paddle, run demos to prospects and utilise relevant client examples.
  • Increase sales productivity and ensure sales and marketing alignment on go-to-market and sales strategies.
  • Create and drive sales training programs, including product and competitor training and individualised development plans and assess their effectiveness – working with Product Marketing for relevant content and delivery.
  • Overall ownership of sales content (sales collateral, demo decks, case studies - with content provided by Product Marketing, Success, you and others) and own our Sales Playbook to enable rapid on-boarding and continuous development.
  • Work closely with the VP of Sales, Sales Managers and Sales Operations to map sales processes, measure performance, and make recommendations for improved sales efficiency and effectiveness.
  • Manage and oversee the on-boarding of new members of the team, providing a successful induction to the company and a faster ramp-up period.
  • This will include our UK and US-based sales professionals.

We'd love to hear from you if

  • You have solid experience in sales enablement within a complex software company, ideally including SaaS or B2B products.
  • You are competent in and excited by the use of data to drive success in outreach and sales.
  • You have a track record of coaching sales organisations and working with Sales Management to help ramp them to full quota.
  • You have project managed or supported cross-departmental initiatives from the sales-team perspective, such as product marketing, sales automation, sequencing and templating.
  • You have past sales experience, ideally in the role of an Account Executive, working on complex enterprise sales in a software/ SaaS business.
  • You have provided great on-boarding to new members of the Sales team and have worked to refine and improve onboarding programmes.
  • You have experience working in a startup environment (Pre-Series C; under 200 people)
  • You acquire technical acumen and have past management experience

Why you’ll love working at Paddle

We are a diverse team of around 120 people and we care deeply about enabling a great culture which is inclusive no matter your background. We celebrate our diverse group of talented employees and we pride ourselves on our transparent, collaborative, friendly and respectful culture.

We offer a full slate of benefits, including competitive salaries, stock options, pension plans, private healthcare and on-site coaching sessions. We believe in flexible working and offer all team members unlimited holidays and 3 months paid parental leaves regardless of gender. Plus we offer some not-so-standard, extra-fun benefits, which can include anything from joining office football team, or enjoying a board game night. We host regular company get-togethers and quarterly socials. We have weekly catered lunches and of course and fully stocked fridges. We value learning and will help you with your personal development where we can — from constant exposure to new challenges and annual learning stipend to regular internal and external training.


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