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Sleepless Media optimises proposals and creative assets

This full-service web design and branding agency needed a way to track and organise their client proposals, master service agreements and design sketches.

They found an intuitive solution with DocSend and Dropbox.

7 people sit and stand around a beach bonfire on a starry night


Sleepless Media is a full-service web design and development agency that provides innovative brand experiences anchored around custom, responsive websites. Developing creative assets for a large client base including Levi Strauss, Lenny & Larry’s and Breeo, Sleepless Media relies on both Dropbox and DocSend to securely share project proposals and creative files with prospective clients.

The Challenge

Prior to DocSend, Jon Cattivera, CEO and Creative Director, would send partnership proposals and creative files to clients as email attachments. As his client list grew, Jon needed a more scalable solution to better control the proposal process. Additionally, he needed a more robust platform that would allow him to customise and organise design elements.


Jon turned to DocSend to securely send and track sales proposals to prospective clients and Dropbox to share creative files.

Advanced insights into client proposals shorten sales cycles

As a creative professional managing a design and web development firm that caters to leading global brands, Jon juggles many different responsibilities in order to provide the best possible customer service. Following up at the right moment with a potential client is critical, especially when closing new business. However, operating on limited time, Jon must be deliberate and thoughtful when sharing project proposals and reviewing statements of work from potential clients. Previously, Jon had no intel into whether prospective clients were reviewing proposals he would send out. ‘I had no idea who was interested in working with us after those initial conversations. I wanted a better sense of whether prospective clients were serious about partnering with us,’ Jon shared.

After trying out DocSend’s free trial, Jon immediately felt the impact of using DocSend’s document analytics. Now, Jon knows exactly which prospective clients were genuinely interested in collaborating through real-time email updates and notifications when they are viewing project proposals. Additionally, Jon can see whether individuals have forwarded over his files to the right people at the company. Instead of spending tedious weeks searching for the right person to connect with, Jon can uncover the right person and follow up accordingly. ‘DocSend shows us who other core decision-makers are, which has given us back much-needed time to focus on what we do best – quality creative design and development.’

‘DocSend shows us exactly which prospective clients are engaging with proposals and are interested in working with us. I love how the email notifications alert me when someone is reviewing a proposal in real time, which helps me prioritise strategic follow-up and insight on any potential questions.’

- Jon Cattivera, CEO and Creative Director, Sleepless Media
Jon Cattivera of Sleepless Media

Intuitive presentations build stronger client relationships

Potential clients could often be looking into multiple agencies, so it is important for design and development firms to stand out among the competition. Jon is able to rely on DocSend to display custom proposals in a professional manner, which gives his agency a unique advantage. ‘I present my proposals directly in DocSend because I’m usually sharing just my browser and not my whole screen. DocSend lets me go back and forth between a website and my PDF all in one window, instead of having to flip back and forth to try and find the right file outside of a browser, or having to share my entire screen.’


Easily executing master service agreements with eSignature

As a nimble and growing design and creative development firm, Sleepless Media works with a range of clients with specific visions, often reflected in the statement of work. Jon was overjoyed when he found out that he could execute master service agreements and statements of work with DocSend’s eSignature feature. ‘I had previously looked into DocuSign, but it was too clunky. I really needed a simple way to execute client agreements,’ Jon shared. Once a client agrees to partner with Sleepless Media, Jon sends them their contract to sign directly in DocSend. ‘Clients can easily review their proposal and execute their agreement in one product experience using DocSend’s eSignature, without switching back and forth between different, bulky software,’ Jon shared.

Additionally, milestones and deliverables can sometimes change for those in the creative space. Managing different change orders for a long list of clients can be tricky, but Jon is able to organise all executed client agreements in DocSend folders.

DocSend’s eSignature makes the negotiation and close process intuitive for both us and our clients. I’m able to add in necessary fields and send out critical agreements that allow us to build long-term relationships with our clients.

- Jon Cattivera, CEO and Creative Director, Sleepless Media

Storing client branding assets and creative in Dropbox

Working with a wide range of businesses requires keeping close tabs on all of their creative files. Jon relies on Dropbox Business to organise all of his client logos and core design elements. Once a brand signs on to work with Sleepless Media, Jon will create a Dropbox folder containing everything he will need for their partnership. ‘With so many different clients, Dropbox makes it easy for us to quickly find any creative element we might need for a project. Dropbox holds all of our Sketch files, heavier design files and branding assets,’ Jon shared.

No matter where team members are located, members of the Sleepless Media group are able to work flexibly and make changes to creative files in Dropbox. In an industry where creative adjustments often come up, Jon and his team keep all files up to date securely with Dropbox’s cloud storage. Relying on both Dropbox and DocSend, Sleepless Media continues to secure partnership agreements and provide innovative web designs for a growing list of clients.

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