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 customize and organize design elements.

The Solution:

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 prioritize strategic follow-up and insight on any potential questions.

Jon Cattivera

CEO and Creative Director, 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 e-Signature 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 softwares,” 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 organize 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 organize 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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The Center for Management & Organization Effectiveness (CMOE) is a learning and development consulting group that works with individuals, teams, and organizations to provide customized workshops, offsites, speaking engagements, and consultative research. Providing solutions to organizations like Northern Trust, JB Hunt, Siemens Energy, Zendesk, Amazon, and Shape Technologies, CMOE relies on DocSend to securely share documents and presentations with prospective clients during the sales process.

The Challenge

Prior to DocSend, Mark Parkinson, Vice President of Sales Enablement at CMOE, would send out sales presentations and proposals to prospective clients as email attachments. With an impressive library of growing presentations, Mark and his sales team wanted to find a more organized sharing solution that would provide them with more control over the sales process.

The Solution:

The team turned to DocSend’s secure document sharing solution to manage all documents shared during the sales cycle.

Seamlessly sharing sales proposals and presentations

Managing a pipeline of prospective Fortune 500 companies requires meticulous attention to detail and focus. It is critical to know exactly when proposals were sent out and what materials prospective clients can access. For Mark, email attachments were outdated and did not represent his organization in the best light in front of major companies. It simply wasn’t professional to include multiple attachments on an email, which could also get stuck in spam filters or never reach prospects.

When Mark first explored DocSend, he was excited by how he could more securely organize client-facing documents in a way that was more intuitive for clients to access. CMOE has an impressive library of content as part of their consulting packages and Mark often shares previews of presentations with prospective clients, so they can get a taste of CMOE’s learning and development offerings. These presentations contain intellectual property that Mark did not want to get into the wrong hands. With DocSend’s secure sharing capabilities, Mark can easily add an email verification or passcode, so that only approved prospective clients can access the materials. Additionally, Mark can set expiration dates, so that prospects can only access the content during an allotted period, like during an active sales cycle. “DocSend gives us more control over our documents, which is crucial in a fast-paced sales environment,” Mark shared.

To ensure that prospective clients know exactly where to find all CMOE presentations relevant to their needs, Mark created over two-hundred individualized content portals to house client information using DocSend Deal Rooms. While hundreds of individualized client folders might sound like a lot of time to create, with DocSend, Mark can easily duplicate a deal room template in less than a minute. “I’ve templatized four different deal rooms based on our four different product offerings. When a client shows interest in one product offering, for example, Applied Strategic Thinking, I can duplicate that deal room and include a customized sales quote. Creating a personalized, visual representation of content helps us provide the best possible customer experience,” Mark shared. In addition to presentations that address the prospective client’s primary area of interest, Mark also includes statements of work and individualized pricing proposals in each personalized deal room. Whereas email attachments could come off as an informal or tedious experience, a clean, customized deal room with CMOE’s logo and banner gives prospective clients reassurance that CMOE is an organization they could trust.

I would never build a sales technology stack in the future without DocSend. This genre of tool is huge. Salespeople have never before had visibility into their prospects’ actions outside of a tool like DocSend.

Mark Parkinson

Vice President of Sales Enablement, CMOE

Uncovering decision makers with document analytics

Among one of the many challenges sales organizations face is determining who is the right decision maker to sign off on a deal. Before using DocSend, Mark had a tough time figuring out the right person to speak with in order to seal the deal. “Nine times out of ten we were talking to someone who is talking to other consulting organizations and presenting findings to a decision maker,” Mark shared.

Mark now has more visibility into where his documents are going with DocSend’s analytics and can use those insights to his advantage. “The beautiful thing about DocSend is I can now see who gatekeepers might be forwarding pricing proposals to, which lets me get a better idea of who the final decision maker is, and be able to connect with the right person at the right time,” Mark shared. By identifying the final decision maker earlier on in the sales process, Mark can get the right information in front of the right person and ensure that CMOE is top-of-mind for prospective clients.

Whereas our competitors might be sending many bulky attachments over email, we are relying on DocSend as an amazing presentation tool to show-off our offerings. The way you can click into a file and view it in a browser is incredible. I’ve had prospective clients tell me they went to a meeting with their vice president and showed them our DocSend link and they were instantly sold on going with us because of how professional and organized it looked.

Mark Parkinson

Vice President of Sales Enablement, CMOE

Framing a conversation with a data-driven approach

Before DocSend, Mark had little visibility into whether prospects were consuming the content he shared with them. While Mark did have insights into whether an email was opened, he had no idea whether a client was looking through their proposals. The only information Mark could rely on was the initial prospective meetings, which left him in the dark most of the time.

Now, Mark can see how prospective clients are engaging with the materials he sends. “After sending out presentation decks and sale proposals, I can see, for example, if prospects are looking at the pricing page and for how long. This can tell me if they might be concerned about pricing, so I can address that in our next call,” Mark shared. Using data to his advantage, Mark can approach conversations with prospects, anticipating any questions or concerns they might have. Mark adds, “Before a call, I’ll jump into DocSend and search a person’s name and see their content consumption data. Seeing everything they’ve looked at helps me frame a conversation.” The key to consultative selling is to predict your prospective client’s needs and provide them with as much information as possible to make an informed decision. Mark can more accurately forecast potential deals each quarter and gauge their interest using DocSend analytics.

It’s great knowing whether a prospect has opened a document and how long they have spent on our pricing page. Having this level of visibility in the sales process is something that I have never had before using DocSend. It provides predictability as to whether a prospective client is interested.

Mark Parkinson

Vice President of Sales Enablement, CMOE

Looking forward to the future: customizing prospective client portals

As Mark continues to utilize DocSend as a sales tool within his organization, he is hoping to try out more customization options in DocSend Deal Rooms. “I’m excited to customize banners and add prospective client logos to their deal rooms to give them even more of a personalized feel,” Mark shared. Providing that individualized touch can go a long way when forming relationships with new clients. DocSend makes it simple for sales professionals like Mark to go the extra mile when creating proposals remotely.

Additionally, Mark is eager to test out the new deal room update notification when adding new materials into content portals. “Having the ability within DocSend to notify prospective clients when I add information to their portal is excellent. It will help me continue to provide value to a prospect and remind them about an earlier conversation we had with helpful information, which might grab their attention, or even reengage a stale lead,” Mark shared. Mark now has more control over his relationships with prospective clients, allowing him to bring all that CMOE has to offer to even more organizations.

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Before using DocSend, 104 West organized and managed media relations across different lists, Google Drive folders, and documents. Maintaining a running list of pitches, press drafts, and media kits per client was both tedious and time-consuming. “As an Account Manager, I’m always striving to provide transparency to our clients of our pitching process and status. The pitching progress we can share with clients is pretty black and white. We either pitched and didn’t hear back or we pitched and received a response. This leads to a decent amount of hypothesizing on our part to determine when and how it’s best to follow up with the media contacts we don’t hear from,” shares Laura Kubitz, 104 West Account Manager.

When pitching a story to a targeted list of media who could be a good fit for a story, reporter interest and pickup depends on a number of things including a compelling story, an existing working relationship, and of course, chance. Timing, current projects, and the news cycle can all impact media interest and inclusion in a story. 104 West utilizes DocSend to host the content they are pitching, such as a press release or piece of content, using a unique trackable link per story so they have aggregated analytics into the amount of interest a particular pitch is experiencing. This allows 104 West to anticipate the expected interest or on the other hand, if a new angle should be tried or a different group of media should be pursued.

“Now with DocSend, I can provide a much more tangible and accurate status report of our pitches to our clients. For example, has the media looked at the pitch, how much did they dig in, and even if they shared it with colleagues. This then empowers us to strategically approach certain media based on how we know they’ve interacted and proactively propose the best next steps,” said Laura.

One simple and secure link for maintaining and distributing client media kits

104 West maintains their client’s media kits to ensure that the imagery and copy that’s published about each client is the most accurate and up-to-date. Previous to DocSend, Allison Heard, 104 West’s Creative Services Manager, would maintain a Google Drive folder per client and at times even per media outreach, in order to ensure that the relevant stakeholders saw all of – or only – what they should see. With Google’s limitations in user provisioning and secure sharing, this led to having to manage multiple media kits per client based on the pitch. At other times, media kits were shared as an email attachment but many times the files were too large causing delivery issues and lag time or confusion during a critical time.

“At times, we only want to share a certain video or custom graphic with the media. Alternatively, one media contact we may want to share a different level of detail with than another. So we would find ourselves creating multiple folders for a single client pitch, which then created internal confusion and led to issues with a single source of truth,” recalls Allison.

“With DocSend, we’re able to easily maintain our client’s media kits in Spaces – a central, secure place. The link is always live and up-to-date, so I no longer have to worry about media having an outdated logo or incorrect boilerplate, and we can also provide different levels of access or custom views to different sets of media contacts. This is a game-changer for us when it comes to ensuring we have the right information in front of the right folks,” shares Allison.

104 West manages their client’s media kits in DocSend

Managing an embargoed story through secure sharing

For 104 West, managing embargoed stories can be tricky when sharing a highly anticipated or highly classified bit of information or upcoming story. Prior to DocSend, this was managed over email either with an attachment or Google Doc link. Although Google Docs is great for real-time editing and collaboration, when it comes to securely pitching highly anticipated information, a link or PDF attachment in the wrong hands can ruin a story’s debut.

“With DocSend, we can protect the security of our embargoed pitches by requiring an email in order to view it. Even if that link is forwarded to someone else, we are notified of that and they also can’t view it without providing their email. This not only gives us a great peace of mind that a story can’t leak but also provides us insight into the media’s interaction and consumption of our timely pitch,” shares Brian Mast, Managing Partner, 104 West.

“With DocSend, we have real-time insights as to which part of our story resonates – or not. With these insights we are building better relationships with the press and providing better transparency, media strategy, and overall service to our clients.

Brian Mast

Managing Partner, 104 West

A new lens into client and media relations

With DocSend, 104 West is now able to more proactively manage media relationships as well as provide their clients with more detailed and specific insight into their pitching process and strategy. With real-time, secure sharing, tracking and maintaining of client assets, 104 West is able to spend more time nailing the story angle than playing the follow-up.

“DocSend has transformed the way we pitch and share information with the media. The best way for us to work with the media is to give them relevant and valuable information. We now have real-time insights as to which part of our story resonates – or not. With these insights we are building better relationships with the press and providing better transparency, media strategy, and overall service to our clients,” concludes Brian.

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