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From Dealbreaker to Dealmaker: What We Learned at ACC’s Deal or No Deal

November 12, 2019 6 min read
2019 ACC Deal or No Deal Speakers Namely Optimizely Ironclad
(L-R) Namely Contract Ops Advisor Cecile Quesada, Optimizely Sr. Legal Counsel Halsey Bertenthal, and Ironclad GC Chris Young

There’s a perception that Legal is where contracts go to die. When you’re racing to the finish line, stopping for legal review can slow your momentum to a crawl. In the rush to meet quota, sales reps can become frustrated with Legal — sometimes avoiding them altogether and putting their organization at risk should a deal go wrong.

The reality is modern legal teams are dealmakers who are empowering their sales teams to generate revenue responsibly

On Nov. 7, Optimizely’s senior legal counsel, Halsey Bertenthal, and Namely’s contract operations advisor, Cecile Quesada, joined Ironclad’s general counsel, Chris Young, at the ACC San Francisco Bay Area’s annual Deal or No Deal conference to share practical tips for aligning legal and sales processes to facilitate company growth.

The following are highlights of their discussion:

Build the relationship

We think of sales as a monolith but actually it’s a collection of individuals. Establishing a healthy relationship between Sales and Legal can help deals close faster — and on policy. 

Approach for partnering with Sales

  • Spend the time to get to know your reps. Bertenthal likes to look out for a deal she can work on with someone to begin building their trust. 
  • Stay on top of deals. AEs love to quarterback their own deals. Quesada recommends that if you know that a deal is coming down the pipe, raise your hand, and stay on top of it — if you’re ready to negotiate with them, that will build trust fairly quickly.
  • Speak in layperson’s terms. Young recommends conducting a sales training that covers legal provisions and clauses in layperson’s terms. Review the meaning of clauses, why provisions are more negotiated than others, and the consequences of agreeing to some different clause. This helps “deputize” sales reps to look out for terms and proactively flag issues.

Training Sales 

  • Ensure you have multiple touch points throughout the year. From day one, Optimizely’s legal team meets with a new rep and ensures Legal is part of ongoing sales training and quarterly updates. With at least seven interactions across the year, Legal is able to build a stronger relationship with their sales partners.
  • Connect with the right people and communication channel. At Namely, the legal team makes it a priority to get to know and build trust with the person responsible for sales enablement. They also follow the right communication channels, such as a weekly email sales update, to ensure legal has visibility of any important updates or changes. 

Executive leadership

  • Leverage data. The most fruitful discussions at Optimizely happen before the end of quarter crunch — and they rely on data to advise leadership when there’s friction from the sales team. For example, Legal can get buy-in from sales leadership when they can show that deals move and close faster processed on their own paper versus third party paper. 
  • Hold execs accountable for adhering to policies. At Ironclad, the GC and VP of Sales are both veteran in-house counsel and share a lot of empathy for each other. They talk candidly about norms, processes and protocols for each of their teams. That way, they are aligned on holding their direct reports accountable. If a sales rep heads in a different direction, the leaders are able to connect openly and swiftly resolve issues. 
  • Have execs lead an all-hands on deck approach to meeting sales goals. At Namely, everyone in the company strives to close the EOQ/EOM strong. The CFO, COO or CEO will send communications two weeks before plus a final reminder the Monday before EOM to ensure all senior leaders are ready and willing to remove roadblocks on business or product decisions. 

Aligning with Sales

Even if you have a healthy relationship with the sales team, some reps may ignore the policies and practices that Legal has instilled for the sake of convenience and expedience of satisfying quota. Legal can mitigate risks by providing clear guidelines for Sales and get involved in contract negotiations early and often.

Challenges to aligning with Sales

  • Maintaining a positive reputation. When people think of you as an enemy, they will spend a great deal of energy trying to avoid you! To counteract this, Bertenthal recommends that you gain timely insight into the pipeline and specific deal challenges, which allows better alignment and partnership during a crunch period.
  • Staying proactive and on top of deals. Recognize that at the end of quarter, emotions can flare and it may seem easier to avoid conflict by bending on policies and negotiations. “Stay firm and stand by your policies,” says Quesada. 
  • Enforcing compliance. At Ironclad, all sales contracts are required to be reviewed and processed in Ironclad. If a sales rep wants to meet their goal, they’ll have to follow the rules.

Setting priorities

For Legal, there’s a dynamic of moving fast yet responsibly, and being close partners and guardians of policy when it comes to priorities. 

  • Implement a system to align priorities. Optimizely’s legal team is plugged into weekly status calls and can access Salesforce reports. They regularly review the delta between what Sales is telling Legal via Salesforce and what deals are actually in their contract management platform to color insights to sales leadership. “If we see a seven-figure deal forecast for end of quarter but haven’t seen the paperwork started in Ironclad, we can predict that the deal won’t close,” says Bertenthal. The more often Legal is brought in to win-and-planning calls, the better they can advise the rep on the deal and provide an opportunity for the salesperson to escalate issues. 
  • Keep an open line of communication. Legal at Namely is actively involved in sales calls and works directly with reps in supporting the negotiation of terms and conditions of their deals. They have a Slack channel dedicated for senior sales leadership — if they haven’t heard back from an account executive on an issue that they previously flagged, then they alert leadership there. 

Sales planning

It’s important for Legal to be part of the sales planning process — inefficient use of your legal resources can slow the sales process, contributing to frustration and increasing outside counsel costs. 

  • Understand the risks siloing your sales and legal teams. “We do not have as many legal resources as Sales does, so it’s important for Namely’s legal team to be invited to QBRs and other planning activities so that we can allocate resources accordingly. The fine print here is determining whether every agreement is worth Legal’s time,” notes Quesada.
  • Planning together helps anticipate volume. If Legal can understand the expected pipeline goal, legal can ramp up support in anticipation of helping to close deals, whether it’s shifting priorities or standardizing contract terms. 
  • Optimize together. Sales and legal leaders should review the previous quarter’s data and adjust discount ceilings accordingly or review friction points to decrease the deal cycle.

Speed and compliance

How do you move quickly but responsibly? Set SLAs for legal review and regularly prioritize agreements in pipeline.

Balancing speed and compliance

  • Review and prioritize tiers of terms and conditions: deal killer, important, preferred and nice-to-have. Optimizely’s Bertenthal recommends looking at the size of the deal, where you are in the quarter and what buckets of things you’re willing to give on. Checklists and playbooks help speed the review of deals as well. 
  • Be super responsive. Legal at Namely strives to stay ahead of sales as much as possible. Enabling technology also helps — they can go as fast as sales if sales is complying with set processes.

Establishing a compliance mindset

  • The fear of the change is almost always worse than the actuality. Call their bluff. When rolling out a contract management platform, Optimizely conducted a training and found that the reps weren’t excited about using a new technology. With the blessing of their sales leader, Legal sat with Sales all day and every day for the last two weeks of the quarter to provide support. The immediate presence of Legal on the sales floor was miraculous — the number of issues dropped to almost zero overnight. The sales team ended up loving the self-service aspect of the contract management platform — being able to execute a sales contract from Salesforce and essentially get deal through faster if the terms were within the guardrails that Legal had set. 

The importance of technology

  • Technology is vital to ensuring alignment, transparency and compliance. Saying “no” creates friction. Quesada finds that technology sets expectations and policies, and removes human roadblocks — essentially removing the emotions around getting a deal done. 
  • Halsey agrees that technology enables compliance with less friction: “Here are the rules, it’s not personal. Instead of an uphill battle, it’s a nice slide to closing the deal.” Not only can a system collect approvals, it can bake in compliance — if someone changes a number or length of time, then it triggers an approval. The system can also show statuses so that teams can work asynchronously. Ultimately technology removes Legal as a roadblock and enables sales to make deals 24-7 globally. 

Parting words

Building trust with your sales organization requires ongoing training and communication to reduce silos and align priorities. Technology can enforce compliance, provide transparency and streamline contract reviews. Ultimately, Legal can help Sales fast track deals responsibly if they are involved in the contract negotiations early and often. 


Learn how Namely accelerated its sales contracting process with Ironclad here. If you’re interested in how Ironclad uses Ironclad from the perspective of a solutions engineer, account executive, general counsel or VP of Sales, check out the “Ironclad is for Closers” series here.

More about Ironclad

Ironclad is the leading digital contracting platform for legal teams. By streamlining contract workflows, from creation and approvals to compliance and insights, Ironclad frees legal to be the strategic advisors they’re meant to be. Ironclad is used by modern General Counsels and their teams at companies like Dropbox, AppDynamics and Fitbit to unlock the power of their contracts data. Ironclad was named one of the 20 Rising Stars as part of the Forbes 2019 Cloud 100 list, the definitive list of the top 100 private cloud companies in the world. The company is backed by investors like Accel, Sequoia, Y Combinator and Emergence Capital. To learn more, visit our homepage.

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